Ranking Every ‘Crazy Ex-Girlfriend’ Original Song #32-1: A “Wednesday” Listicle

Editor’s Note: This list was originally printed as one massive article comparing every Crazy Ex-Girlfriend song, designed to run alongside the series finale. As it turned out, in its massive 250,000 word form, the article overwhelmed the servers and was rendered unreadable. So I have decided to break the article up into four individual parts, as well as an overall list that will compare the 128 without videos or write-ups. You can find that list, as well as links to each article, at the bottom of every post, as well as under the Sacred Wall GOATs tab at the top of the page, because that’s what this show is: the Greatest Of All Time.

Tonight, one of the greatest shows of the 21st century comes to an end. Crazy Ex-Girlfriend, Rachel Bloom and Aline Brosh McKenna’s surreal, comedic look at gender dynamics, romantic comedy tropes, musical comedies, and mental illness, has been one of the most joyful creative endeavors I’ve ever seen, and one with the most challenging premise. Following Bloom’s Rebecca Bunch as she upends her cushy-but-mentally-unhealthy New York law career in order to move across the country to be near her high school boyfriend that she hasn’t seen in ten years, the show plays with tropes in both classical theater and modern romantic comedies, as well as music – did I mention that Rebecca’s undiagnosed borderline personality disorder convinces her that major moments in her life are, in fact, extravagant Broadway musical numbers? Yes, over the course of four seasons and soon to be 61 episodes, Crazy Ex-Girlfriend has written exactly 128 original songs – and that’s not including reprises and bit-time one-offs. Each song, written by a team of Bloom, her longtime writing partner Jack Dolgen, and “That Thing You Do!” and “Stacy’s Mom” writer Adam Schlesinger, is a masterful, hilarious takedown of a specific genre, explores some sort of universal notion or story trope, be it an ode to motherhood to the intricacies of dating. So in honor of this Friday’s series finale, I thought I’d undertake the weighty task of Ranking Every Crazy Ex-Girlfriend Original Song!

In order to actually complete this task, I’m going to have to set up some ground rules. First, there’s no such thing as a “bad” Crazy Ex-Girlfriend song. Every song produced by this show is somewhere on the sliding scale of “good,” and therefore each song’s placement is simply a matter of meeting my predetermined criteria. And what is this criteria? Well, each song has to answer a specific question pertaining to different musical techniques: prowess (does the song stand on its own outside of the show?), performance (how committed is the actor singing the song?), comedy (how smart is the spoof of the artist/genre/song?), lyrical complexity (how satirical/smart/silly is the song?), and context (how well does the song fit into the episode/arc?). The songs also get bonus points for how well the music video is produced and how poignant is the song’s resonance. And finally, just a few housekeeping rules, to help things move along more smoothly. First, all reprises are ineligible. I don’t care how funny it is when Trent sings “I’m Just A Boy In Love” or how good “Settle For Me” is, each song can and will only be counted once, with one exception: if the song actually changes and evolves from its predecessor (see: “Who’s The New Guy?” and “He’s The New Guy”), it will be allowed to stand on its own. Next, any episode that features the same song performed over a period of time as a vignette, the song will only count as one. This means “Santa Ana Winds” will only count as one song, despite being several miniature bits performed by Eric Michael Roy. And finally, no theme song is eligible for the list. Instead, I will be ranking the four variations of the theme song…right now!

  1. “Crazy Ex-Girlfriend” (Season One)
  2. “Meet Rebecca” (Season Four)
  3. “I’m Just A Girl In Love” (Season Two)
  4. “You Do/Don’t Wanna Be Crazy” (Season Three)

Well, now that that’s all settled, it’s time to finally get to the rankings. Who knows what’s going to happen? Which season has the best songs? How many times will Donna Lynne Champlin make the Top Ten? And will my unhealthy love for Santino Fontan, Skylar Astin, and Greg Serrano as a character cloud my judgment to an unhealthy level? I think it’s time we find out.

32. “The Buzzing From The Bathroom”

The best – and perhaps most horrifically scarring – of the show’s Les Mis parodies comes in a way that no one was expecting. As sung by Michael McMillan’s Tim, this parody of “Empty Chairs At Empty Tables” tackles a different type of guilt and remorse – the realization that Tim, who thought of himself as a gifted lover to his wife, has not been satisfying his wife’s needs. As the song goes on, Tim sadly realizes that the reason he would always hear buzzing in the bathroom after he and his wife had sex was because she needed to, um, finish the job. The reason this song is so great is not because of the lyrics (but don’t get me wrong, they are spectacular – “That damned, incessant hum! I used to think I was her hero/Can’t believe she didn’t come!”), but because of how dedicated McMillan is to the joke. He plays it exactly like Eddie Redmayne in the infamous movie, from the lip quivers to the close-ups to the dramatic high notes. It is…truly something, and only a show like Crazy Ex-Girlfriend would dare write it, let alone pull it off.

 

31. “Greg’s Drinking Song”

If you were to think about it too hard (too, too hard), “Greg’s Drinking Song” would be a truly depressing reality. The confessions Greg makes about his realized alcoholism are truly sobering (pun not intended), and this is a truly harsh wake-up call for the characters of the show. But that’s what Crazy Ex-Girlfriend does so well: it takes terrifying real-life illnesses and finds the humor in it as a means of destigmatizing and openly addressing these serious issues, Mel Brooks style. The irony of Greg singing a drinking song to talk about alcoholism is brilliant, and the list of things that he does while drunk grows more and more grotesque as it goes on (and for good reason). While other films and shows may risk romanticizing alcoholism by having its characters get into wacky mischief, Crazy Ex tackles the issue with the maturity of A Star Is Born and Leaving Las Vegas: Greg pisses his pants, pukes on his cat, threatens his boss, and forces planes to emergency land by charging the cockpit – not to mention has sex with a bush. Musically, the song is incredibly catchy, and the list grows more and more terrifyingly real with each revelation. At the end of the day, this is exactly what Bloom, Schlesinger, and Dolgen do well: they tackle real-life issues with brains, maturity, and a wicked sense of humor.

 

30. “Oh My God I Think I Like You”

“Oh My God I Think I Like You” is one of Season One’s funnier songs. An Enya parody that’s decidedly un-Enya in its lyrics, the song tackles the confusing realization that one goes through when they realize that the person they’ve been hooking up with “casually” is someone they genuinely care about. As Rebecca slowly realizes she has feelings for Greg, she comes to the horrific realization that “Oh my god, I think I like you!” And in case she was unsure about that, she goes on a long tangent about imagining “marrying him on a hillside surrounded by ducks/and then getting into a row boat.” The sequence is humorous because Rebecca continues talking about the emotional side of the relationship through her song while physically, she and Greg continue to have all sorts of crazy sex (including a couple of hilariously well-timed physical gestures to avoid pissing off the censors). In one of the funniest pieces of wordplay in the show’s history, Rebecca hypothesizes getting protection not for the sex, but for love (“Are there condoms that can prevent these feelings? Is there an IUD that can stop the image of you and me?”). It’s a clever song, well constructed musically, and could easily be played on the radio if it just weren’t so envelope pushing. In short, it’s a perfect Crazy Ex-Girlfriend showstopper.

 

29. “Maybe She’s Not Such A Heinous Bitch After All”

Rebecca Bunch’s relationship with her mom is not the best. That was established in the pilot, and it was a major theme throughout the run of the show. Perhaps the best exploration of this notion (other than a certain song in the Top Ten) comes in the Season Three episode “I Never Want To See Josh Again.” When Rebecca comes home to her mother, deep inside her shame spiral, her mother is her normal self, criticizing and mocking her daughter. That is, until she finds a website on suicide methods on her daughter’s computer (unrelated to this list, but the way Feldshuh says, “Becky, no” upon seeing this is one of my favorite moments from the run of the show). After that, she begins actually nurturing her daughter and giving her the loving relationship she’s always craved. And thus launches Bloom’s spot-on The Ronettes/“Be My Baby” send-up “Maybe She’s Not Such a Heinous Bitch After All.” Featuring such hilariously dark lines like “I don’t want to bash her head in with this cup” and “For once, I don’t wish she had a cancerous mole” (which even horrifies the background singers), the song is perhaps one of the weirdest, yet funniest tributes to the complicated relationships between mothers and daughters.

 

28. “I’ve Got My Head In The Clouds”

It was during “I’ve Got My Head In The Clouds” when I first realized that Vincent Rodriguez had been short shrifted the first few seasons of the show. A spirited send-up to Gene Kelly, the song is the perfect commentary on Josh’s mental understanding of both the world and religion. It’s easy to interpret the song as a critique of religion in general – Josh openly states he’s using the priesthood and faith to escape from reality. However, the song has less to do with the actual church and more to do with Josh trying to use his Catholicism as an escape as opposed to a tool for help and comfort. Want proof? Look at his tap dance with the Holy Ghost. When the Ghost is revealed to be a man in a sheet, Josh asks “Whoa, that’s what you look like?” The Holy Ghost replies, “It’s what you think I look like.” This is sharp commentary on people who try to use religion not as a tool to help themselves and others, but to escape from responsibilities and real action. This is sharp, funny commentary, and Rodriguez sings the hell out of it. The song also gives Rodriguez a chance to demonstrate his impressive dance abilities, from tap to gymnastics to a general sense of athleticism, and for that I will forever be thankful.

 

27. “I Want To Be A Child Star”

“I Want To Be A Child Star” is a jaw-dropping moment from the first half of Season Four, smack dab in the middle of a string of jaw-dropping moments. Performed by guest actor Luca Padovan, the song is a parody of the lifestyles of child stars like Lindsay Lohan and Justin Bieber. As Tucker Bunch, Padovan describes his dream of becoming a major star – but not just the general sense of celebrity. He wants the entire ordeal, including the tragic downward spiral that follows fame. He wants to be a “pre-teen Hollywood trainwreck,” one that will have his brain warped on his trip to prison, that will sue his parents for emancipation “after they get caught stealing from me,” and eventually end up in a bar where people say, “Hey, there’s that bloated bankrupt creep.” As he sings about this horrible spiral, Padovan performs a spot-on child star dance sequence, including coming down into the audience to sing to a thirteen-year-old girl. This joke has been explored everywhere, from Popstar to The Other Two, but never has felt as alive and as harrowing as it does here. The song by Schlesinger is pitch-perfect, and the lyrics by Dolgen are shocking, and when coupled with Padovan’s performance, “Child Star” becomes one of the greatest “can’t-miss” moments in the history of the show.

 

26. “Gettin’ Bi”

We’re into the home stretch, folks! And I can think of no better way to kick off the final 26 than by talking about “Gettin’ Bi,” Pete Gardner’s Huey Lewis-inspired Pride song. Upon realizing that he’s bisexual, Darryl holds a (quite unnecessary) meeting of his employees to officially come out. What could have been a silly or dorky number (and yes, it is both of those things too) ends up becoming a powerful anthem about accepting yourself, wholeheartedly embracing Darryl’s bi-identification. It’s exhilarating to hear Darryl proudly declare, “I don’t know how/I don’t know why/But I like ladies/And I like guys.” Does he give away a little too much information, like his reveal, “Being bi does not imply that you’re a player or a slut/Sure, I like sex/But I’m no ho, I take things slow?” Sure, but it’s all in good natured pride (and he’s called out, appropriately, by Paula, who whispers, “please make him stop” in terror). And the song does away with the myth that being bi is being stuck between straight and gay, and “you should just go gay all the way,” which made millions of Americans scream out at once, “Thank you!” “Gettin’ Bi” is one of the show’s most important songs, and it’s made all the richer thanks to its impressive musicality and smart lyrics.

 

25. “I Hate Everything But You”

Skylar Astin’s Greg really didn’t get that many solos – he was mostly in a series of reprises, as well as “Hell, Nice To Meet You.” But when he got his one big chance to shine, “I Hate Everything But You,” he made sure to pull out all the stops to make it the hit it deserved to be. A spot-on Bruce Springsteen parody (right down to the handkerchief he keeps in his back pocket), Astin’s Greg does his best to explain to Rebecca the delicate balance between Greg’s hatred for most of humanity and everything around him and the inexplicably strong love he feels for her. The titular chorus, “I hate everything but you,” is oddly romantic, but it’s hard to focus on that, because even Greg’s too caught up listing all the things he hates. And that’s the beauty of both the song and the performance – it’s just a list of nuisances that we pessimists (a friend texted me during this performance and yelled, “It’s you!”) find to be hate-worthy. This list ranges from people who enjoy flowers to basic people who use the hashtag “mood” to people who say “zing.” However, even as Astin freaks out over the joy of listing everything he hates, or the reveal that he (and perhaps even Springsteen) doesn’t know how to play guitar and he just holds it for style, he remembers the reason he’s making this list in the first place – to tell Rebecca, in his own f*cked up way, that he loves her, and that he can’t explain why he loves her, and that while he’ll try to like things for her, he can only change himself so much. And that is the thing he hates the most. You know, other than guys who name their cars.

 

24. “Heavy Boobs”

According to Bloom, she has been working on certain lyrics from “Heavy Boobs” since she was a teenager. It certainly shows, as the Beyoncé inspired “Heavy Boobs” is one of the funniest, most painfully honest songs in the course of the show. The song, as sung by Rebecca to Valencia (and really, all small-breasted women of the world, and men who try not to think about these things), is an exploration of the realities of having double or triple D breasts. While it is true they can fill out dresses and shirts better than most women, it is often forgotten how heavy boobs really are (they are, after all, “just sacks of yellow fat”). They could blind someone if they were hit in the face with them, you can’t run very far with heavy boobs, and they collect things that fall into them all the time (“When I go to bed at night, it’s like opening a Mary Poppins bag”). Rachel’s (and my) favorite part of the song comes when things get slowed down so Rebecca can explain the “dense like dying stars” metaphor – specifically, how if a Red Giant doesn’t have enough mass to fuse carbon, then carbon and oxygen build up to create a white dwarf (“essentially, my boobs are like a white dwarf”). It’s a funny, catchy, memorable song that tops all the criteria I’ve set forth, and it’s one of the best songs Crazy Ex-Girlfriend has ever done.

 

23. “What’ll It Be?”

It should come as no surprise to most readers that I’m a huge f*cking Billy Joel fan. So it should be even less of a surprise that my favorite character, Greg Serrano, performing a Billy Joel send-up would rank high on the list of best Crazy Ex-Girlfriend songs. The strangest – and most memorable – thing about “What’ll It Be?” the show’s send-up to “Piano Man,” is that it’s not a comedic song. In many ways, it’s almost dramatic. “What’ll It Be?” is about the realization that you’ve outgrown your hometown, but circumstances both in and out of your control have trapped you there, surrounded by people you know you’re smarter than who have moved on with their lives. It’s a true tragedy (just like “Piano Man”) about self-loathing and realizing it’s time to grow up and go on with your life. The song features some truly poignant lyrics like “I know this town like the back of my hand/But I’m not such a fan of the back of my hand” and “Am I doomed to stay here/Pouring my high school friends beer/For the rest of eternity?” This is the perfect song for Greg, sung with proper angst by Santino Fontana, it stands out as one of the most unique, truly great songs in the history of Crazy Ex-Girlfriend.

 

22. “Feeling Kinda Naughty”

A parody of Katy Perry’s “I Kissed A Girl,” “Feelin’ Kinda Naughty is a hilarious parody of the delicate line between love, hate, and obsession. As Rebecca idolizes Josh’s girlfriend Valencia to an unhealthy degree, she talks about her “girl crush” on her new “friend” (and future real friend). The song starts off innocent enough, but the dark undercurrents are revealed in the chorus, as Rebecca reveals that instead of cute pillow fights and innocent kisses, she wants to “Lock you in a basement with soundproof walls/And take over your identity.” From there, things get worse, as Rebecca slowly reveals her desire to both idolize and destroy her romantic rival, commenting that she wants to “Kill you and wear your skin like a dress/But also have you see me in the dress/And be like ‘OMG, you look so cute in my skin!’” The music is insanely hummable, instantly getting stuck in your head, and yet the lyrics make you afraid to sing it out loud, lest people think you’re a serial killer. The kicker comes at the end when Rebecca reveals she wants to take measurements of Valencia’s body, then go up to a surgeon, “Make my body like your body/Like that film with Liberace,” and for a split second we see Rebecca dressed as Michael Douglas’ Liberace from Behind the Candelabra. This is a terrific song from the show’s second (!) episode, and the fact the music video remains so watchable this far into the show’s run is a testament to its staying power.

 

21. “Let’s Have Intercourse”

Scott Michael Foster’s debut song is one of those moments that would have been talked about at the water cooler Monday morning if this was the nineties. A parody of Ed Sheeran’s Wedding Anthem “Thinking Out Loud,” the song says everything you need to know about Nathaniel’s character in two-and-a-half minutes. As Nathaniel realizes that he has weird, unexplained feelings for Rebecca, and they find themselves trapped in an elevator with no hope of rescue, Nathaniel proposes the two have sex. In an incredibly seductive number (represented by a ballroom routine, performed with a clearly irritated Rebecca), Nathaniel proceeds to neg her as he tries to explain his emotions. Including such details as “Unfortunately I want to have sex with you/I don’t know what happened, maybe you lost some weight” and “You and I are both highly intelligent people/Although I am in much better physical shape.” What makes this song (and, eventually, the performance) so great is the way Foster delivers his lines. He is such a gifted performer in terms of facial cues that he can make any line funny, even while performing it with the cockiest, straightest delivery you can possibly imagine. It’s a tour-du-force performance, and one that immediately got every fan onboard with the prospect of Nathaniel as a love interest (even if I am, to quote Valencia, “Still Team Greg. Obviously.”).

 

20. “The End of the Movie”

“The End of the Movie” is a punch to the gut, an existential awakening for an audience that may or may not even fully want to understand existentialism. Having spent the episode thinking herself the hero of her own Scary Sexy Lady Movie, Rebecca realizes that life is, in fact, not a movie. Real life is too chaotic to be a movie, and there are far too many characters for everyone to be a main character. Even worse, there is no way that Rebecca can be the hero – not after kidnapping Josh’s mom, not after tormenting Josh, and especially not after sleeping with Greg’s father, Marco (who, to quote Nostalgia Cat, “flipped her like a pancake”). No, real life is a nightmare, not a movie; it is just a series of revelations that eventually lead to the grave. Still, there are a few moments of comedy to be found. The rhyming scheme intentionally drops out when the singer explains that “Life doesn’t make narrative sense.” And the funniest part of the song has to be when you realize, halfway through, that the singer is one of those “extras in life”: Josh Groban. That’s right, Groban shows up for the final song of the episode, only to be revealed as a background singer who then berates Rebecca for her terrible decisions. A dark piece of comedic philosophy, “The End of The Movie” is one of the most mature songs in the show’s run, and it easily deserves this spot in the Top 20.

 

19. “I Love My Daughter”

“I Love My Daughter” was a seminal moment for Crazy Ex-Girlfriend. It was one of the first times the show branched out to allow a side character to not only strut their stuff, but to critique a genre through satire while simultaneously tackling the tricky nuances of life. Pete Gardner absolutely knocks the hell out of “I Love My Daughter,” a sweet country song that slowly devolves into a nightmare as Darryl realizes that his loving descriptions of his daughter sound creepy to the outside world. Based on a country song titled “Butterfly Kisses” in which the singer may, in fact, want to f*ck his daughter, “Daughter” works because as Darryl continues to put his foot deeper into his own mouth, his doubling back makes it clear that he’s just a loving dad who doesn’t express himself well. It’s a character choice that, as Bloom has noted in interviews, has made fathers across the land look at their daughters and say, “That! That’s what I’m feeling!” There’s an alternative version of this song that could have been creepy, playing up the pervertedness of it all – and had original Darryl Michael McDonald (not that one) played the role, it’s entirely possible that it would have, and Darryl would not be the sensitive hero he is today. But thanks to Gardner’s quiet, loving performance, the song becomes an ode to the awkwardness of language and love, and it becomes the massive success that it is today.

 

18. “Face Your Fears”

Donna Lynne Champlin’s first real solo on Crazy Ex-Girlfriend, “Face Your Fears,” is a masterful tour-du-force. A gospel homage, “Face Your Fears” is one of those inspirational power ballads one would hear from Aretha Franklin or Whitney Houston. However, because this show is far too silly to allow a pure inspirational ballad on unchecked, writers Bloom, Dolgen, Schlesinger, and Sono Patel undercut each piece of Paula’s advice with the revelation that the cocky, unchecked bravery is a surefire way to get killed. Starting out simple enough, Paula advises that “If someone pulls a gun on me, I pull out my knife.” Things get worse from there as she advices “If you’re in a burning building, take a deep breath and stay right there” and “If a bear comes at you in the woods/Go up to the bear, put your hand on its chest and say ‘Bear, I’m not afraid!’” And just when you think the advice couldn’t get any worse, Paula brings in a backup children’s choir – running in, armed with scissors, and trimming dangerously close to their own necks. Paula and her choir advise reaching for the stars and “Literally touching a star/Because stars aren’t that hot.” It is a silly, dumb, wonderful number. At the heart of it all, however, is Champlin, singing her heart out with the voice and bravado of all the legends that came before her, and doing it complete justice. This is a legendary moment in the show’s run, a powerhouse musical sequence, and easily one of the best the show has ever done.

 

17. “Sexy French Depression”

Some of my favorite moments on the show (hell, there are three in the Top Twenty, as far as I can tell) are the moments when the show comically explores the realities of feeling depression. One of the first of these types of songs is the French parody “Sexy French Depression.” Annoyed by the media’s glamorization and romanticizing of depression and mental illness, Rebecca’s subconscious sings a “realistic” French depression ballad (think Édith Piaf). While originally a list of “sexy” attributes of depression (dark eyes, heaving bosom, red lips, etc.), the song takes a turn as it begins to explore the nitty-gritty of it all. “My bed smells like a tampon,” she notes, before continuing on to reveal that she “blacks out on dessert wine.” However, the funniest moments of the song come when Rebecca begins to sing in French, with the subtitles revealing her worst decisions: “I bought a book about John Wayne Gacy online;” “I go through old AOL Instant Messenger conversation with my college boyfriend;” “Oui, je suis garbage.” The funniest, darkest moment comes when Rebecca begins to rapid fire the nonstop flurry of dark thoughts running through her mind, so fast that the subtitles can barely keep up. Any person who has ever suffered depression will tell you that this is exactly what it’s like when you’re going through depression. “Sexy French Depression” is, far and away, the most underrated song the show has ever done, and I want to make sure it gets the credit it deserves.

 

16. “(Tell Me I’m Okay) Patrick”

Another great depression anthem, “(Tell Me I’m Okay) Patrick” is a solid send-up to the era of Burt Bacharach. As Rebecca’s wedding day approaches, she finds herself breaking down to her deliveryman, Patrick (guest star and Bloom’s former boss Seth Green). The song balances the humor and pain of being mentally unwell perfectly, as Rebecca asks – nay, begs – for assurance from the put-upon UPS man that she is “Ok.” You see, she “thinks” she’s fine, but she’s “only like 43% sure.” In her need for validation, she admits she doesn’t understand how to be a normal person, assuming that she was “sick the day in school they taught that.” And as she grows more and more unstable as the song goes on, she begins to threaten Patrick, declaring “Is there a manual? Do you have a manual? I know you have a manual, Patrick! I know it’s in your truck!” My favorite moments in the song are the quick cuts to the piano. When we first see the scene, Patrick confusedly plays piano as Rebecca sits on top of the piano. When next we see them, they have switched roles. And in the goofiest return of the lot, both Rebecca and Patrick sit upon the piano while Patrick’s deliveries play the piano for the two of them. The visuals may be goofy, and Rebecca’s meltdown funny, but make no mistake: this is a serious, heartfelt song that connects with anyone who fears that there may be something seriously wrong with them. It’s a terrific number for Bloom, and a showstopper for the show.

 

15. “West Covina”

The very first number in Crazy Ex-Girlfriend history, “West Covina” is one of the best numbers the show has ever done. It is the first moment when Rebecca breaks from reality (or finally embraces her true calling; depends on how romantic you are) and hears the music in the world around her. It’s the moment where she officially leaves her New York job where she made dough, but it made her blue to fly across the country to West Covina. As the song goes on, she admits that Josh also lives there, but “that’s not why she’s moving there.” As she begins to feel the need to defend her decision, the music slowly amps up, and Bloom’s tremendous performance becomes more and more manic (“Look everyone, stop giving me the shakedown/I am not having a nervous…”). The song plays with rhymes and signage to make comments on Rebecca’s mental state, and jokes about marching bands having their budgets slashed play like gangbusters. Perhaps best of all is the fact that “West Covina” is wholly original. It’s not a parody of anything, it’s not a pastiche. It’s just a simple, full-hearted Broadway send-up, a musical ode to the theatre nerds who hear show tunes in their heads year-round. This is a stellar, overwhelmingly great moment, and the image of Rebecca riding the giant pretzel into the sky declaring “Only two hours from the beach!” will go down in pilot history alongside Tony Soprano collapsing next to his grill, Rachel Green bursting through the diner door in a wedding dress, and the arrival of Agent Cooper in the town of Twin Peaks. That’s right, that’s how good this pilot is.

 

14. “Let’s Generalize About Men”

“Let’s Generalize About Men” is the first time we heard the foursome of Rebecca, Paula, Valencia, and Heather. And guess what? There is no better group in the entire cast than Rachel Bloom, Donna Lynne Champlin, Gabrielle Ruiz, and Vella Lovell. A send-up to the Weather Girls and The Pointer Sisters, “Let’s Generalize About Men” is a hilarious critique (or at least it was, the show came out a week before Harvey W*instein) of the way women, after a bad breakup, will group together to group all men together and critique them on gender stereotypes. This is a smart song all around, from comments about “high-fiving each other over a bunch of blanket statements” and how “all men are emotionally stunted.” The women also humorously comment on their own complicity in bad behavior, as Rebecca asks, “How come men never listen and only think about themselves/As opposed to women who always listen and never think about themselves?” The satire becomes sharper as they begin to stereotype gay men, and especially in the climax when they declare “All men are murderers and rapists,” and Paula becomes despondent as she remembers, “I have sons!” As I said, top-notch satire. And, as I said before, these women can harmonize. Seriously: this is a terrific sounding song, and it’s one of the most replayable of the entire repertoire. The costumes are flashy, the dancing top-notch, and the music top-of-the-line – all the ingredients of a Top 15 Crazy Ex-Girlfriend song.

 

13. “It Was A Sh*t Show”

In my own fantasy dream world, Santino Fontana never left the cast. He stayed around for the entirety of the run, he bettered himself, and he and Rebecca lived happily ever after. Unfortunately, this is not my dream world. On the bright side, if it were, we wouldn’t have gotten Fontana’s top-notch send-off, a Frank Sinatra tribute (“My Way” style) about admitting to yourselves that the breakup was, indeed, terrible. Given the blunt title “It Was A Sh*t Show,” Fontana leaves it all on the line as he describes how their relationship, while sexually charged and filled with love, resembled “Jerry Springer, not Casablanca,” and that their relationship made “Chernobyl look like a campfire, and Hurricane Katrina look like bad weather.” And while Greg is tempted to stay, he knows that, for both their sakes, he needs to sacrifice his feelings and let them both move on. It’s a powerful testament to all those relationships in our lives, the ones where we desperately love the person but know, deep down, that it is inherently toxic, and that there truly is no endgame for the two of you. And while you have to move on and save yourselves while you still can, you’ll never forget “This beautiful, heart stopping, breathtaking, life changing…” well, you know.

 

12. “After Everything I’ve Done For You (That You Didn’t Ask For)”

I still remember watching the Crazy Ex-Girlfriend Season One finale live in my college dorm room. And I remember it because I remember loudly screaming “YES!” when Paula launches into her full-on Mama Rose impression for “After Everything I’ve Done For You (That You Didn’t Ask For). The song works on two levels. On the surface (and not to be overlooked), it’s a terrific anthem for Donna Lynne Champlin, allowing her a moment to cut loose and belt once more before the season ended (and belt she did. Holy sh*t). However, beyond that, it also showed audiences just how far down the rabbit hole Paula was willing to go, both to help her friends as well as to give herself another dose of joy in life. We hear all the sordid details about the things we took for granted throughout the season. How did Paula know so much about Valencia’s schedule? She blackmailed her boss into letting her make the schedule. How did she know how to get Rebecca named a bridesmaid? She followed Josh’s mother around and “bumped” into her at Starbucks. At the core of it all is underlying theme that Paula subconsciously thinks of Rebecca as a daughter, and that’s why she went to these lengths. It’s a terrific song, sung with fire and brimstone levels of passion by Champlin, and it closed out Season One on a high note (alongside “One Indescribable Instant,” of course).

 

11. “F*ckton of Cats”

While I can’t, in good conscience, put “F*cton of Cats” (and yes, I’m using the naughty title, because it is much funnier than “Buttload”) in the Top Ten, I must admit that this song has everything I could ever want in a Crazy Ex-Girlfriend music video. An old school Rachel Bloom goofy meltdown? Check. A quartet with the Girl Group? Check. A premise satirizing the cliché of the Crazy Cat Lady? Check. ACTUAL PUPPETS TO MAKE THE CATS SING ALONG WITH REBECCA?!? Oh God, you bet your sweet ass there’s a check. That’s right, “F*ckton of Cats” is a goofy ass song about Rebecca’s resignation to Cat Lady status, planning to head over to the “Lonely Lady Cat Store” to buy literally every cat they have. She joyously enters and sings about her love of her newfound pets, despite the background singer cats (all played by giant, unrealistic cat puppets) clearly remaining skeptical and uninterested in her. As Rebecca walks off to make the sale, the cats then take over, lamenting their status as “symbols of loneliness,” and threatening to ruin Rebecca’s couch, making her loneliness worse, and hating Rebecca’s favorite magazine, The Atlantic (which Rebecca admits recently wrote that organisms in cat poop make you crazy). This is a silly song at its heart, a song that works both in musical and visual form, and one that never ceases to put a smile on my face. Oh, and while the cats sing their solo, Rebecca uses a scratching post as a washboard. This show is brilliant, and I’m so sad to see it go.

 

10. “JAP Battle”

Woo hoo, Top Ten, Bunch-A-Friends! And I can’t think of a better way to kick that list off than with Season One’s “JAP Battle.” The Hamilton-esque epic features Rebecca facing off against her arch-rival since preschool, Audra Levine. Played with vicious gusto by Rachel Grate, Audra is every bit a match for Rebecca, with the two delivering a show-stopping musical number about their shared Jewish history, their family’s hatred, and using their knowledge of each other to deal cruel blows upon each other’s self-esteem in the Jewish American Princess Battle. Bloom is passionate in her performance, giving a great performance and adding her own spin to her lines, like the revelation that she banged Audra’s fiancé back in college, and “Really not hot at all/Small dick, rotten lay.” However, the real star of the song is Grate, who not only sings the hell out of it, but has such great facial cues and vocal inflections it’s impossible to take your eyes off her. My favorite part of the song is the way her eyes go wide and her smile disappears as she says, “Like you’re gonna lose this lawsuit.” The song is also a real “Who, What, and Where?” of Jewish American culture, name-dropping ultra specific New York locations and Jewish vocabulary to drive home the frenemy and faith-based relationship between the two women, driven apart by overbearing mothers. This is a shining moment for the show, musically and performatively, and I can’t think of a better way to kick off the Top Ten.

 

9. “I Could If I Wanted To”

Famously the song where Jack Dolgen declared, “Oh, don’t worry guys, I got this,” “I Could If I Wanted To” was a defining moment for Dolgen, Fontana, and the character of Greg. A send-up to grunge, Nirvana, and The Verve, “I Could If I Wanted To” is a nihilistic anthem about the revelation that smarts might not actually be enough in this world. Greg’s ego crushed, he tries to shrug it off with his cocky brand of nihilistic self-loathing. In a stunning one-take, Fontana walks the streets of West Covina, declaring that he just “doesn’t care” about anything in the world around him, but if he did, he would be great at it. “I could if I wanted to,” he shouts angrily. From getting an A on a test to dealing stocks to being able to throw a ball, to commenting on how “This song sucks/I could make it good if I wanted to!” Fontana adds a little bit of “mustard” (to borrow an old showbiz term) on each line, giving it a unique spin filled with humor and angst. The final reveal, when he tells a woman in a crowd that he could “swallow a sword if he wanted to,” and she calls him an idiot, it just icing on the cake. This is a stunning moment, one of Greg’s best, and easily worthy of the Top Ten.

 

8. “Where’s The Bathroom”

Few moments over the course of the show have been as dramatic or as mesmerizing as Tovah Feldshuh’s introduction to Crazy Ex-Girlfriend. “Where’s The Bathroom” is the perfect patter song, a commentary on overbearing, judgmental mothers and the whirlwind nature of their arrival when they come to visit. Feldshuh milks every lyric she delivers, including “By the way you’re looking healthy/And by healthy I mean chunky/I don’t mean this as an insult/I’m just stating it as fact” and “God I give you everything and still you just want more!” It is clear from the conversation that Naomi enjoys needling her daughter, and she knows exactly how to push her buttons. What’s most impressive about both the song and Feldshuh’s performance is the way it slowly, smartly gets faster until the song is borderline stream-of-consciousness – something anyone with a parent like this can confirm is accurate. Feldshuh’s performance on this song is easily in the Top Five performances from the show (even if the song is only #8), and once you hear it, it is impossible to get “Where’s The Bathroom?” out of your head. Oh, and a late-in-the-game reprise by none other than “Weird” Al Yankovic is pretty great, too!

 

7. “Maybe This Dream”

I limited myself to two Paula solos in the Top Ten, because any more would just feel like cheating. And it wouldn’t feel like a proper Top Ten without an appearance from “Maybe This Dream,” a f*ck you to any casting directors who didn’t feel like the ever-talented Donna Lynne could play a Disney Princess. “Maybe This Dream” is perhaps the greatest Disney Princess song in two and a half decades, with the exception of “Let It Go,” and certainly since “A Whole New World.” As Paula faces the prospect of all her dreams coming true (i.e. officially getting her law degree), she sings about her dreams finally coming true, despite life’s efforts to bring her down. Her observations, sung with a Disney Princess level of sweetness, note that “Maybe this dream/Won’t poop on my face/Like a seagull at the beach!” and the much blunter “Maybe this dream/Won’t be like my vibrator/Breaking when I need it most!” The song is the perfect mix of sweet and uplifting with more than a dash of sass and cynicism mixed in for good measure. Champlin knocks it out of the park, adding every ounce of charm and grit she has to capture the hopes and dreams of a person who has long since given up. It’s one of the show’s more iconic songs, and as should be expected, its star cast member absolutely crushes it.

 

6. “Don’t Be A Lawyer”

If you’d told me before this season began that a song performed by side character Jim would break into my Top Ten, I would have laughed at you. Yet here we are, in a world where the magical “Don’t Be A Lawyer” exists. Taking the form of a Bobby Brown parody, “Don’t Be A Lawyer” is Jim’s testament to the true awfulness of a legal degree. From the crippling law school debt to the reveal that you’ll be spending your days working on a “pharmaceutical company’s merger with another pharmaceutical company,” Jim breaks down each and every way the profession will disappoint you. Featuring such great lines as, “Just say no to the lawyer employer” and “There are so many other professions/That don’t turn you into Jeff Sessions,” and danced with unheralded zest by Moseley, the song is an unexpected gem, and by the time “The CW’s” lawyer comes out to read a disclaimer, grows despondent, and jumps out a window, your jaw will be on the floor, watching in awe. Shortly after the song’s release, I played it for a friend of mine who is just finishing up law school and has been working in a law office. He didn’t really laugh as it played, only chuckling at “lawyer employer.” At the end, I asked if he just didn’t find it funny. His response? “Oh, no, it was funny. It was just so…real.” And that, my friends, is the power of “Don’t Be A Lawyer.”

 

5. “Friendtopia”

My love of the girl group numbers is well-worn at this point, but it’s time we address the OG itself (sans Paula, sadly), “Friendtopia.” A blatant Spice Girls parody, and sung in wonderfully fake British accents, “Friendtopia” arrives at the moment Rebecca realizes that, for the first time in her life, she actually has friends. And inspired by Taylor Swift’s infamous “Squad,” she and the girls plot their own world takeover. The best part of the song is just how giddy Rebecca, Valencia, and Heather are together. As the terrific send-up to “Spice Up Your Life” and “Wannabe” starts to play, the trio alternates between their normal plans, like going to the local sushi place, not getting in, and declaring, “Let’s just go home and drink rosé,” and Rebecca’s vision of world domination, like the effortlessly brilliant line, “We’re gonna braid each other’s hair, then cut each other’s braids, connect the braids, to build a rope, to hang all of Congress!” This is a funny song, effortlessly parodying the world conquering nature of popular girl groups as well as the overwhelmingly positive feeling of finding your first group of best friends. And it’s filled with hidden gems of moments, from Valencia’s spirited reading of the line, “Czar of torture” to the end of the song declaring the trio’s love of the cult film Hocus Pocus (this was a laugh out loud line for me). “Friendtopia” is perfect satire, a perfect parody, and one of the best songs on the show.

 

4. “You Stupid Bitch”

When “You Stupid Bitch” came out, I was in a depression spiral of my own. And I do not exaggerate when I say that I played this song, on repeat, over 300 times. And I also do not exaggerate when I say its message of “self-indulgent self-loathing” helped me get through one of the lowest points in my life. “You Stupid Bitch” is an honest to God miracle of a song, the perfect embodiment of the human mental state at the height of depression. Performed as a Barbra Streisand torch song, Bloom gives her all to the voice inside her own head, insulting her for ruining the perceived only good thing in her life. As the song builds to its chorus, Rebecca begins to berate herself – “You ruined everything, you stupid bitch! Lose some weight!” As she continues to pity and insult herself, she begins to play the audience, Streisand style, for confirmation of her own awfulness. The greatest joke in the song is when she encourages the audience to sing along, declaring, “I deserve this.” It is the perfect metaphor for the way we force others to see us as a bad person when we’re depressed, thus fulfilling our own negative prophesy. Bloom lays it all out on the line with this performance, baring her soul and her own personal demons, and allowing her audience to realize that maybe, just maybe, they aren’t as alone in their depression as they think. And I thank her for that.

 

3. “First Penis I Saw”

And now we come to the greatest Donna Lynne Champlin song of all time, her wonderfully raunchy Season Three opus, “First Penis I Saw.” A spot-on parody of ABBA’s “Mamma Mia,” “First Penis” is a testament to young love, in all its messy glory. As Paula runs into her first boyfriend in the hallways of a grocery story, she reflects on their summer of firsts together, and how he was, well, “the first penis I saw.” Joined by backup dancers, Paula’s lyrics reflect a universal awkwardness about teen love – “a few times before I felt it through his pants/and just generally kind of rubbed it.” And when she reaches the second chorus, right around the time “Jeff took her hand,” she grabs a suggestively sized eggplant to use as a stand-in microphone. This is songwriting at its best – a smart parody song tackling the universal feeling of teenage awkwardness. And Donna Lynne’s performance here is far and away the best of any musical performance on the show to date – she gives a fiery, upbeat, youthful performance that captures the magic of ABBA, the mystery of young love, and the wise mockery of a woman looking back, all mixed in with the singing voice of an angel. In short, this is one of the best musical numbers the show has ever done, and it should be fondly remembered for generations to come as an example of parody and humor.

 

2. “Settle For Me”

I knew from the get-go that “Settle For Me” would be a Top Two song. It’s the moment most fans came into the show, it’s an effortlessly good song, and it’s already an audition hall staple (and I would know, I spend many a lonely night watching these kinds of videos online). As performed by Greg as a last-ditch effort to get Rebecca to go on a date with him, the song takes the form of an old-school Fred Astaire number, complete with black and white cinematography, gorgeous gowns, and a full-on dance sequence. In the song, Greg makes a series of ridiculous puns and reflections explaining his inferiority to Josh while still demonstrating his value. “I’m Rocky V to his Rocky,” he declares. “If he’s your broken condom, I’m Plan B!” There’s even commentary on the way self-loathing like this can take a poisonous form, as he begins objectifying her with terms like, “Shmoopy Pie” and “Sugar Jugs,” as “demeaning terms are all that I have left/Of my masculinity.” It’s a clever, gorgeous song that really changed the game for the show in terms of storytelling and musicality. Fontana really nails the tone of this song, basking in the self-hate the character requires while still earnestly singing his heart out. It’s a difficult balance, but one he makes look generally easy.

 

1. “The Sexy Getting Ready Song”

I’m a sucker for the granddaddies of them all, and for Crazy Ex-Girlfriend, that would be this. The watershed moment in the pilot that declared firmly and decisively that this was a brave, honest, smart, and outright hilarious show. Covering the hilariously awful lengths women have to go through to beautify themselves (as opposed to Greg, who’s asleep on the couch), the song graphically describes every pumice stone, waxing, and bleeding body part, all set to a sexy R&B song. As Rebecca finds herself joined by backup dancers, each adorned with hair curlers, waxed lips, and more accessories, you can actually feel the show coming into its own: talking about a crazy double standard women face, using humor to drive the point home, and delivering it in the form of a music video. The highlight comes when an earnest Rebecca invites Nipsey Hussle (who was tragically killed while I was writing this article) to perform the guest rap, before he stops, horrified at the revelation of what women go through to get ready. He leaves “forever changed by what he’s just seen.” It’s bold, funny, and musically rich, and it easily deserves this spot as Crazy Ex-Girlfriend’s greatest song.

 

Well, that’s the end, everyone! I hope you enjoyed this countdown, and at the very least I hope it gave you lots to talk about! The finale begins at 8:00 pm tonight, so I hope you’ll be watching. Until then, feel free to comment with your favorites down below, or even feel free to challenge some of my rankings. Obviously my list is objectively right, but you can try to change my mind away from science if you want!

You can see the full list by clicking on this link right here, or you can read each individual part by clicking on one of the links below:

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