Ranking Every ‘Crazy Ex-Girlfriend’ Original Song #64-33: 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.

64. “The Villain In My Own Story”

“The Villain In My Own Story” is a shocking moment for Rebecca’s personal growth. It is the first time she stops to evaluate her actions, as she realizes that the only reason we’ve been rooting for her is because she is our protagonist – from an outsider’s perspective, she’s the villain. A parody of “Poor Unfortunate Souls,” she slowly realizes she’s the evil witch, or the ice queen trying to break up Kate Hudson and Matthew McConaughey. The added joke is that Rebecca is fully aware that the song she is singing is evil, and questions why anyone (looking at you, Alan Menken) would write something so sinister. It’s both a funny song and a great send-up to Disney Villain Songs.


63. “I’m So Good At Yoga”

Gabrielle Ruiz really couldn’t have asked for a better introduction to the Crazy Ex-Girlfriend universe. “I’m So Good At Yoga” is one of my funniest, smartest songs on the show, and if it had had a stronger impact, I probably would have placed it higher. A commentary on the fear that your romantic rival is better than you in every way, as well as a Bollywood send-up, “I’m So Good At Yoga” is a tour-du-force by Valencia. Alternating between praises of herself, like “I do sh*t with my body that no human should be able to do,” and insults of Rebecca, like “F*ck you, you’re fat” and “I’m not afraid of clowns and trains,” the song is hilariously insulting, comically incredible, and ultimately flawless. God bless Gabrielle Ruiz.


62. “Triceratops Ballet”

Another great Ruiz moment, “Triceratops Ballet” is the Dream Ballet for people who hate Dream Ballets. It also calls out their very existence, by writing it into the show by having Valencia and Rebecca accidentally drop acid at a concert in the desert. After that, the song devolves into a ballet sequence between Gabrielle and Vincent (great dancers) and Rachel (a great comical dancer). It’s not quite the most interesting musical moment, although it does feature some solid musical callbacks (especially “I’m A Good Person), but the twist here is Rebecca turning into a monstrous Triceratops when she sees Josh, and Valencia’s heartbreak as her relationship with Josh comes to an end. It also features the single funniest moments on the show: Rachel dressed as a Triceratops chasing Vincent Rodriguez around the set. It is single-handedly one of the funniest visual sequences I’ve ever seen on TV, and it gets massive bonus points for that.


61. “This Session Is Going To Be Different”

She only got three songs over the course of the show, but whenever Michael Hyatt as Dr. Akopian had a solo, it was a can’t-miss moment. In “This Session Is Going To Be Different,” Hyatt is given her Minnelli moment, parodying “Maybe This Time” from Cabaret. The song is great for two very specific reasons. The first is the heartwarming: Dr. Akopian genuinely wants to help Rebecca, and the prospect of her finally turning a new leaf and working on her issues (instead of ignoring every piece of advice she’s given) is an exciting, fulfilling promise. The second reason, however, is the comedic: as much as she wants to help Rebecca, the bulk of the song is talking about how terrible a patient Rebecca is, from her constant committing of crimes to her inability to work for change, the fact that she now turns down health insurance because Rebecca’s such a nightmare, and how if she doesn’t change, “I f*cking quit.” It’s a show-stopping performance on Hyatt’s part, and the jokes land – the perfect ingredients for a great Crazy Ex song.


60. “Group Hang”

I didn’t quite realize I needed a Shakira parody from Crazy Ex-Girlfriend, but that’s exactly what “Group Hang” does: it fulfills the needs I didn’t know I had. The song has three general premises, all playing out at the same time, and humorously. The first is the general commentary: the awkwardness of trying to flirt/rebuild a relationship when the other person has invited their friends for a “group hang.” Watching Rebecca awkwardly trying to fit in with the group is painful, especially as her attempts to piggyback off stories always involves death. The second is the fact that Rebecca can’t even focus on the group hang because the restaurant’s design is so unusual (it’s a Mexican restaurant that doesn’t really serve Mexican food) that she feels gaslighted and can’t stop talking about it. And the third is the Shakira parody, where she finds herself caught off-guard by the ever-changing green screen behind her (especially when a horse pops up, which she is terrified of). It’s a weird, quirky little song, but Bloom sings the hell out of it, and it is musically brilliant.


59. “Dream Ghost”

“Dream Ghost” is our second song by Dr. Akopian, and for good measure, she brought along Ricki Lake and Amber Riley. A send-up to Dreamgirls, the song takes on the ultra-meta format of a dream musical sequence inside a dream, as Rebecca passes out from sleeping pills on a flight to New York and imagines a Ghost of Christmas Past-style advisor in the form of her therapist. Ghost Dr. Akopian’s song (backed up by other dream ghosts) explains the concept succinctly and humorously, in perfect Crazy Ex fashion: she’s either a metaphor or real, because “it’s more interesting that way,” and the ghosts show up to help people make decisions, ranging from the serious (“This guy is deciding whether or not to leave his wife”) to the silly (“This douche is agonizing over whether to buy or lease a new Porsche”). And in case the general conceit wasn’t comical enough, we learn that Dream Ghosts are women “because they don’t pay or provide benefits,” a tragic, hilarious piece of commentary.


58. “No One Else Is Singing My Song”

“No One Else Is Singing My Song” works for two very clear reasons. A ballad that tackles the way people always believe their pain is unique, despite everyone having similar doubts and fears, the song is a trio between Rebecca, Nathaniel, and Josh. The comedy of the song comes from how they essentially sing the same song about singing solo, including “specific” observations about being by people who are asleep, or the way they try to change the rhythm to prove their alone, all at the same time. But what I like about this song is the way it grows from the three of them to the entire ensemble, including Paula, Valencia, Hector, and even Grocery Clerk With Half An Eyelid, which creates a unique group number as well as drives the point home that everyone shares these fears and anxieties. It’s a sweet, smart song that really works both in and out of context. Bonus points for how into it Gabrielle Ruiz gets. She didn’t have to overplay it that much, but she did it. She did it for us.


57. “We Tapped That Ass”

“We Tapped That Ass” is one of the only two Emmy-nominated songs from the show’s run (#JusticeForCrazyEx). And honestly, while there were better songs from Season Two, it makes sense. It is a joyously upbeat, smartly sung-and-danced by Santino Fontana’s Greg Serrano and Rodriguez’s Josh Chan, and lyrically rich. A send-up to Singin’ In The Rain’s “Moses Supposes,” the song references the lingering reminders of past relationships after a break-up. Here, visions of Greg and Josh remind Rebecca (through a hilarious tap dance number) of all the places they had sex with her, ruining her house for her forever. The song includes hilariously terrible puns, a horrific fake plastic butt, and some terrific choreography from Kat Burns. And when Xander, the vegan guacamole maker Rebecca had a fling with in the fourth episode shows up to declare “I also tapped that ass all over this house!” it cements this moment as an all-time great for the show.


56. “Our Twisted Fate”

“Our Twisted Fate” is a weird song to review. On the one hand, it doesn’t necessarily work as well without the visual gag. On the other hand, the visual gag and the performance by Adam Schlesinger are so good, there’s no way it can’t be in the upper echelons of Crazy Ex-Girlfriend songs. A Simon and Garfunkel parody about the misery of life for a pretzel as eaten by Rebecca Bunch, the song is a spot-on parody of the melancholic folk songs as well as an opportunity to utilize two pretzel puppets, who come to life to sing. It’s one of the funniest, best parody songs the show has ever done – and I cannot stress enough, it is from the perspective of pretzels. Bonus points for the pretzels’ Paul Simon eyebrows and Art Garfunkel afro.


55. “One Indescribable Instant”

Crazy Ex-Girlfriend has openly made reference to its influence from Disney movies, and “One Indescribable Instant” is its most clear inspiration. A parody of Disney songs to the point that it is, allegedly, an in-universe Disney song from the movie “Slumbered.” It works in the show’s context as a metaphor for Rebecca’s childish views on love, as well as the swoon-worthy moment where Rebecca and Josh finally get together at his sister’s wedding. However, it works better as an all-out Disney song in its own right, from the over-the-top (yet never comedic) declarations of love to the song being performed by none other than Lea Salonga, aka Princess Jasmine herself. While “One Indescribable Instant” gets a two on the comedy scale, it gets a ten in both prowess and performance, earning it a spot in the upper echelons of Crazy Ex songs. (Side note: the moment in the Season One finale where Rebecca sings this song to a bird, and the bird’s annoyance is translated for the audience is one of my favorite sequences of television this entire decade).


54. “I Gave You A UTI”

Now that we’re into the upper echelons of songs from the show, let’s talk about Santino Fontana as Greg. Greg was a major focus of the show not only because he was, for many fans, Rebecca’s one true love, but because Fontana brought something unique to the performance. He shared Rebecca’s sense of self-loathing, but the way Fontana filled that loathing with such joy, and with such notable vocal inflections made him a memorable fan favorite. A great example of this is “I Gave You A UTI,” a Nathaniel Rateliff & The Night Sweats parody where Greg takes joy in discovering that he and Rebecca have had so much sex in the first few days of their relationship that she has developed a UTI. The song is embarrassingly blunt and hilariously graphic, and Rebecca’s response is somewhere between flattered and disgusted by lyrics such as “I’m so good at sex, your maiden ship got wrecked” and “If it hurts to take a leak, well that’s just part of my technique.” It’s so dorky and so joyous, it’s impossible to hate – just like Greg himself.


53. “Research Me Obsessively”

“Research Me Obsessively” is the Facebook stalking anthem. Sung by guest actress Brittany Snow, the sequence is a pitch-perfect (I’m so sorry) send-up to “Good For You” by Selena Gomez. In it, Snow’s Anna comes through the computer to convince Rebecca and Valencia to go to extraordinary lengths to find out everything about Josh’s new girlfriend. Things start out mildly harmless (“Look at my Instagram, but it’s private”) before slowly getting worse and worse (“Use the name and picture of someone who went to my high school to set up a fake Instagram/And hope I remember that person a little bit”) until the duo are actively spending money to find out more and more about her. The funny thing about the song is that, even with its dark, dark message, it could still be a radio staple should the show ever go that route. That’s how good the music by Schlesinger and the performance by Brittany Snow are: they made a song about stalking someone a radio-worthy hit (and let’s be honest, The Police already did it, and no one thinks that’s weird).


52. “Fit Hot Guys Have Problems Too”

As tragic as it is that David Hull’s White Josh never got a full-on solo, at least he can take solace in how truly wonderful his duet with Scott Michael Foster turned out to be. “Fit Hot Guys Have Problems Too” is a master class in comedic singing and dancing. A strip tease in a gay bar the two came to escape their problems (both men have recently been dumped), the two take umbrage at the claim that they can’t have problems because of how hot they are. And so begins one of the funniest songs from the course of the show, where the men praise their own bodies while talking about how sad they are (“We both have almost no body fat/But we’re too bummed out to talk about that”). The song works both because of the amount of crying, the carefully choreographed stripping and thrusting, and the looks on Foster and Hull’s faces as they extenuate certain inflections (Foster’s ability to make a face rivals Ruiz’s ability to deliver a line). It’s one of my favorite sequences of the show, a staple on my iPod, and one of the best songs from the show.


51. “This Is My Movement”

“This Is My Movement” is often forgotten due to its appearance late in the episode where Rebecca has attempted suicide, but don’t let that stop you from listening to it. Gabrielle Ruiz’s song, a defense about being “full of crap,” is a full-on Sara Bareilles/Rachel Platten parody about the powerful anti-suicide movement she’s created. The catch is that the song is exclusively poop puns, including “Can’t stop this movement! It’s coming out fast/in a powerful blast!” and “It’s a big fat stinky movement!” Sure, there’s not much more to it than poop puns, but also, it’s a song that’s exclusively poop puns. And Gabrielle Ruiz revels in every minute of it. I don’t care what you say, that’s worthy of a spot at #51 on this list.


50. “The Cats Metaphors”

The first of two collections of songs on this list, one of my favorite moments from the final season of the show has to be the extended Cats parody that came at the start of 2019. Based around a herd of feral cats roaming West Covina, as well as Rebecca’s hatred of the musical Cats – well deserved, I might add – the episode features a litany of famous actors and singers playing different “cats,” a psychological representation of the needs of Rebecca’s, erm, personal cat, if you catch my drift. Each cat has a different mood, and each parodies the randomness and musical stylings of the musical. There’s Riki Linhome as Hungry (Horny Cat), Fred Armisen as Itchy Cat, the Yeast Infection representative, Todrick Hall as Funky Cat, and Megan Amram as Nostalgia Cat (Grizzabella), who is accompanied by Jack Dolgen’s acting debut, the Doggy Dog. The parody is great, the songs sharp, and it serves as a hilarious rebuke to one of the strangest phenomenons of the 1980s.


49. “Sex With A Stranger”

“Sex With A Stranger” features some of the funniest lyrical work the show has ever done. A parody of Ciara-style soul, the song takes place as Rebecca takes home Jason, a “sexy stranger” from the club for a one night stand. However, due to her discomfort around the whole ordeal, she starts putting off the affair by asking a series of important questions, killing the mood but emphasizing the need to address these issues for women. These observations include, “Hey sexy stranger, come back to my place/And please don’t be a murderer!” and “Have you been tested for STDS/Then, waited the three month window…Most people don’t know about the window!” The humorous climax of the song comes when Rebecca declares that Jason’s “balls” (in-universe a pair of Baoding balls, but we all know what she means) smell weird. This is a great song that asks the important questions, like “Is that a gun? Oh thank God, it’s just your penis,” and the fact it appears in the terrific “I’m Going On a Date With Josh’s Friend!” (one of the best episodes the show has ever done) makes it all the better.


48. “The Math Of Love Triangles”

Rachel Bloom has a terrific Marilyn Monroe impression, and I’m glad “The Math of Love Triangles” gives us a chance to see it. Scenically impressive and lyrically sharp, the song critiques the way the old-timey seductress was often portrayed as “dumb” and inferior to men. Throughout the sequence, a group of male backup singers dressed as professors try to teach her about triangles, so she can understand how a love triangle works. However, due to Rebecca Monroe’s inability to do “man math,” she shrugs these facts off with puns (“I need to decide which man’s more acute!”) and inaccuracies (“The center of a triangle’s little old me!” “Actually a triangle has multiple centers!”) And one of the funniest parts of the song comes when the overly-sexed Rebecca comes onto her male “professors” and they declare, “Lady, we’re all gay/We get nothing out of this!” It’s a hilarious number that also comments on a genre and era, and it is also centered by Bloom’s remarkable performance.


47. “I Go To The Zoo”

Up until Season Three, Scott Michael Foster had only really had one number (that song comes in at #21). So when he got a chance to deliver a “Hotline Bling” parody in Season Three, he jumped on the opportunity, and it is for that reason we’ve had so many Nathaniel hits over the past year and a half of the show’s run. His song, “I Go To The Zoo,” describes Nathaniel’s typical mood-lifter: going to the zoo, walking around, and bribing Ron the night guard to let him bottle feed a panda cub. The song balances the humorous descriptions of adult activies (“Bitches surround me/I could go all night”) and Nathaniel’s hilarious inner child (“I say ‘what up’ to kangaroos”). The song is delivered with such passionate zest by Foster, and with such innocent lyrics, that it is hard to pass up such a spirited, heartwarming parody.


46. “What U Missed While U Were PopUlar”

Danny Jolles only had two songs during the course of his appearances on Crazy Ex-Girlfriend (three, if you count his original ska piece, which you absolutely should not do). However, while he only had those two moments to truly shine, he made the most of his time. Is he the first choice to make a Gwen Stefani parody song about high school? Not at all. But that’s what makes George’s ode to the joys of being nerdy in high school such a blast. As he walks around praising the different groups, from the Morning News Team that got fired for uncovering the principal’s embezzlement scheme to the band kids, who took advantage of their co-ed label, to the goths who wore all black and “black flip-flops.” Anchored by Jolles’ spirited Stefani-esque dancing and his earnest singing voice, the song was a highlight of the episode “I’m Not The Person I Used To Be.”


45. “Remember That We Suffered”

Well of course the Patti LuPone/Tovah Feldshuh duet was going to make the Top 45. A parody of the Jewish Klezmer, the song is the perfect embodiment of Jewish guilt. Despite being upbeat and happy (all the naïve, sweet Josh can hear), Rebecca remains fully aware that the song is designed to guilt younger Jews into remembering the hard road it took to get here. While LuPone’s rabbi originally sticks to discussions of minor keys and making “the Beastie Boys or HAIM sing about their suffering,” Feldshuh’s Naomi immediately bursts in with the ultimate guilt trip: the Holocaust. Things become more and more of a bummer as the DJ pipes up with “My grandma’s a Survivor,” and room begins listing important moments in Jewish existence, including: “The sweet and the bitter, Streisand and Hitler, Spielberg and Hitler, and Hitler.” It’s the type of dark humor I love, and a revelatory moment in the course of the show, thanks to the performances by LuPone and Feldshuh.


44. “The Moment Is Me”

Vella Lovell’s Heather only had one real solo on Crazy Ex-Girlfriend, but boy was it a real joy. As Heather graduates college and prepares to join the real world, she finds herself transported to an uplifting musical theatre power ballad, filled with clichéd wishes and a meeting with her future self. However, the real joy of the piece is that Heather, a monotonistic, cynical twenty-something hates musical theatre and all that it stands for. So for the entirety of the piece, which 10 out of 10 musical theatre girls (Rebecca included) would kill to sing, Heather forces her way through it, scoffing and grunting at all of the optimistic language. It is hilarious, well-written, and it could not have been better performed by Lovell.


43. “Hello, Nice To Meet You”

“Hello, Nice To Meet You” is the type of quirky pop ballad you expect to find in a romantic comedy. And that’s exactly what Bloom, Schlesinger, and Skylar Astin are going for in the catchy song about reacquainting with an old flame. Set to a series of rom-com clichéd meet-cutes, the She+Him parody about looking past previous wrongs, insults, and incidents to start fresh and perhaps have a new, adult relationship. The jokes about their issues (“I’ve spent years processing my anger;” “You remind me of this guy whom I labeled as toxic”) all land, but the comfort comes from the way they’ve grown as characters and as people (and in Greg’s case, as actors) to be better towards one another. Musically, it’s a sharp song, and along with some great acting, the song helped ease audiences into the mindset that yes, this was indeed Greg Serrano, returned to help finish off the series (of holidays that leads to Valentine’s Day).


42. “Santa Ana Winds”

One of my favorite characters on the show, and one of my favorite songs to boot, is Eric Michael Roy as a metaphorical stand-in for the Santa Ana Winds (and also kind of a narrator). As the infamous winds blow through West Covina and mess with the characters’ minds, Roy appears to narrate the story and sprinkle mischief on the plot, like some sort of devilish fairy. Styled as Frankie Valli – and singing like him, too – the Santa Ana Winds cause things to get “super weird,” specifically for Rebecca by messing with Josh’s allergies, giving her and Nathaniel the same sexy dream, and then trapping them in an elevator so that they’ll end up kissing (“I’m a bit of a prankster, tee hee hee hee. I just want to see what will happen”). Eric Michael Roy is truly remarkable as the Winds, and the song is easily one of the best from the show’s run.


41. “I’m A Good Person”

“I’m A Good Person” could, in a lot of ways, be the perfect example of what this show is like. Rebecca’s go-to anthem, a defense of her own morality, is as messy as she is – it’s narcissistic, it’s grotesque, and it’s so, so catchy. As Bloom dances around Home Base, rubbing her goodness in Greg’s face (which, according to her, is made of a much-worse substance) and pissing off a fourth-wall breaking sound technician, she makes a lot of bold, sometimes horrific statements, including, “My nickname is Mother Theresa Luther King” and “Newsflash f*ckwads, I’m a good person!” The climax comes when she threatens to kill a woman’s husband if she doesn’t call her a good person. It’s the type of insane, hilarious performance that Bloom used to do on YouTube, and it was a defining moment of Season One.


40. “Trapped In a Car With Someone You Don’t Want To Be Trapped In a Car With”

“Trapped In A Car” is perhaps the most impressive parody the show has ever done. A pastiche of the entirety of the Beach Boys’ career, the song comments on those awkward, long car rides we sometimes share with someone we don’t want to be (Lord knows I’ve been there). What’s brilliant about the song isn’t the commentary on the horrible situation (“Now this person’s eating corn chips, where did those come from?” “Just when you think it’s getting better they take off their shoes”). No, the brilliance comes from the way the song, to show how long it feels when trapped in that car, travels through every era of the Beach Boys’ careers. When the song starts off, it’s straight up the California rock era that produced “Fun, Fun, Fun” and “Surfin’ USA.” However, as time passes, the music evolves into the Pet Sounds-era, including a barking Rebecca and psychedelic music. And just when you think the song can’t go on any longer, the ever-optimistic Darryl and Josh show up with bongos to ruin the band’s legacy and turn everything into “Kokomo.” It is a risky, specific musical pastiche, and I applaud them for not just trying, but succeeding in writing it.


39. “Textmergency”

“Textmergency” is one of my favorite moments from one of my favorite episodes, “That Text Was Not Meant For Josh!” It has all the aspects of a great song – a weird sense of humor, solid musical parody, and commentary that everyone can relate to. As Rebecca realizes she’s sent a text to Josh about how much she loves him, she is egged on to go delete the text by a fellow lawyer, a judge, and the two clients from the case she was working on. The group becomes an 80s style hair band (think White Snake), and they perform a rock about sending the wrong person a text in all sorts of situation, including sending your mother-in-law a dick pic or texting your staff about your yeast infection. However, as the song goes on, the group sings, they often get distracted over their disagreement over the better term for this situation – Textmergency or Texttastrophe. And when tensions reach a breaking point, the Ghost of Steve Jobs shows up to reveal that this was his plan all along! It’s a silly, dumb little song with great music and a smart sense of humor. And Jeff Hiller, Ester Dean, Ivan Hernandez, and Briga Heelan all knock the hell out of it, making it an oft-remembered gem in the Crazy Ex-Girlfriend canon.


38. “Strip Away My Conscience”

I’m surprised it took Crazy Ex-Girlfriend three seasons to create a Fosse number. But if the reason it took so long was to figure out how to write a song this great, then it was absolutely worth it. Rebecca’s song of seduction is everything you want a song like this to be: it’s sexy, it’s smart, and above all, the wordplay is unrivaled. As Rebecca comes to Nathaniel for lessons on how to be amoral (much to his chagrin), she offers herself up as collateral, asking him to “strip away her conscience,” “tear away her morals,” and “kiss around my sense of right and wrong (but not on it, it’s sensitive).” Some of my favorite jokes include her comparison of Nathaniel to Professor Snape (which the Harry Potter fan in him appreciates) and the chanting of “innuendo!” after the particularly great line “let me choke on your cocksuredness.” This is a great song, written by some fantastic writers, and it does justice to one of Broadway’s best choreographers.


37. “Anti-Depressants Are So Not A Big Deal”

Bloom has been an admitted fan of La La Land since its release (especially of how impressive the cinematography was, as a fellow musical filmmaker), so it was only a matter of time before the show released its own spoof of the 2016 phenomenon. While it would have been simple for the show to have just done a throwaway number for their big dance routine, they instead used the musical to discuss something as serious as the necessity of antidepressants. As sung by Dr. Akopian to a despondent Rebecca who feels like a failure for requiring medication, the song features a huge dance sequence tackling the common usage and bonding aspect of taking anti-depressants like “Fluoxetine” and “Citalopram” (because “their lawyers wouldn’t let them use brand names”). The song does away with common myths surrounding the pills and informs the audience that sadness is universal, and that treating it with an appropriate medication “isn’t that big of a deal.” As Rebecca finds herself surrounded by multicolored side characters (including Josh’s sister Jayma), a la “Someone In The Crowd,” she joins in the dance up and down the street, “Another Day Of Sun” style. It’s an uplifting song with an uplifting message, and the minute that iconic music kicked in, I knew I was onboard.


36. “We’ll Never Have Problems Again”

“We’ll Never Have Problems Again” is one of the show’s funniest, smartest parodies. A spoof of Soul Train-era disco, the song features Rebecca and Josh joining the Soul Train line as a means of ignoring their past difficulties and looking to the future, perhaps a bit too optimistically. The song features lyrics like “Do you remember back when we had problems?” “Oh man, that was annoying” and “Our love has magically solved them! There won’t be any more in our future at all!” Meanwhile, when Heather tries to snap them out of their delusions, they chide her until she “Soul Trains” her way out (side note: Soul Train Heather is as amazing as it sounds). The song smartly critiques the optimism of couples that had previously broken up getting back together, and reminds audiences trying the same thing that those preexisting problems will never fully go away. And mixed with Bloom and Rodriguez’s spirited performances, this song transcends to become one of the best in Crazy Ex-Girlfriend’s repertoire.


35. “I’ve Always Never Believed In You”

As we get closer to the top of the list, we’re going to be seeing a lot more Donna Lynne Champlin solos. That’s because Champlin has, for the longest time, been the show’s star player. Her remarkable voice and her vocal inflections make every song, be they an Ethel Merman power ballad, a Disney princess anthem, or ABBA, a stand-out moment. And in Season Four, her big stand-out moment was the powerful mother’s ballad “I’ve Always Never Believed In You.” Sung to eldest son Brendan as he reveals he’s joining the Peace Corps (despite being a potential serial killer in early seasons), the song features Paula confessing, through hilarious double-speak, that she was always afraid that he would end up in jail, and that he has surpassed his wildest dreams. The song both undercuts the stereotype of the supportive mother and speaks to the underlying fear that all mothers have that their child will “turn out rotten.” And the way Champlin belts it is just pure TV magic. It may not be the best Champlin ballads, but that’s the beauty of her acting – if this isn’t her best, can you imagine how good those songs have to be?


34. “The Group Mind Has Decided You’re In Love”

“The Group Mind Has Decided You’re In Love” holds a special place in my heart as both a fan and a former high school cast member in Oklahoma! The only true scene where every cast member performs, “Group Mind” is a parody of the way the Internet obsesses over certain characters and wants them to end up together, whether or not it’s healthy for them. Led by Povitsky’s Maya, the song features the entirety of the company showing up to tell Darryl and White Josh that, despite their Season Three breakup, they’ve all decided that they’re better off together. The lyrics are funny and catchy (Tim telling them, “You’re kinda the only two/LGBTQ/People I know, so to me it’s clearly fate!” is horribly funny), but what I’m caught up in is the staging of it all. This is easily the best dance sequence the show has ever done, and the little side references to Oklahoma! are hilarious, from the commentary on the random ballet bits to the fact that Bloom continuously yells small words of encouragement (“With ya, Timmy!”), Aunt Eller style. And as a fellow Cord Elam (i.e. the sheriff who shows up to kill the fun), I wholeheartedly stan every moment Scott Michael Foster is onscreen during this sequence. This is parody at its finest, a funny song to boot, and an all-around impressive piece of choreography. And it deserves to be a Crazy Ex classic.


33. “Miracle Of Birth”

“Miracle of Birth” is one of the most disturbing songs in Crazy Ex-Girlfriend history – and for good reason. As sung by Donna Lynne Champlin, the song is a loving ode to the joys of motherhood. The catch? It’s also a horrifically graphic depiction of the event, including details about the mucus that plugs the cervix, the declarations of “Kill Me Now,” the ripping of the vagina, and the honest fact that you will likely poop yourself in the process of giving birth. All of this plays out as the men in the room (including the doctor) all throw up in horror, and Paula sits upon a Uterus-Shaped Throne. The song features perhaps the greatest rhyme in the show’s history: “Oops, there it went-a/That was your placenta,” which the song reminds women must be discharged “or you will surely die.” And lest you think this lovely song ends on a happy note, Paula makes sure to remind audiences that you will likely suffer post-partum depression, and therefore won’t even be able to enjoy the miracle you’ve just performed. It is a bleak, terrifying song, and yet Champlin sings it so lovingly (and the set design is so horrifying), that it easily becomes one of the most memorable, most incredible songs in the show’s history.

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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