Ranking Every ‘Crazy Ex-Girlfriend’ Original Song #128-97: 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.

128. “I Feel Like This Isn’t About Me”

“I Feel Like This Isn’t About Me” isn’t necessarily a bad song, it’s just…it’s filler. The entire joke exists around the premise that Cornelia, Rebecca’s replacement at Whitefeather & Associates, is fully aware that the characters are projecting their feelings toward Rebecca onto the poor no-nonsense newcomer. Bayne Gibby commits to the song, and the digression halfway through about just leaving to get Brazilian food is funny, but the song never evolves past a funny, filling pastime to counteract Rebecca’s downward spiral.

127. “George’s Turn”

Danny Jolles didn’t get a lot to do in the first season of Crazy Ex-Girlfriend, but boy did he break out onto the scene after his character, George, is fired in season two (and then rehired, refired, rehired, and then ironically becoming his moody boss’ best friend). The song’s too short to really register on the list, but I love a “Rose’s Turn” tribute, and Jolles is dedicated to the performance. It deserves credit just for that. Oh, and I love the sudden smash cut to the commercial break right after he declares that he “won’t be ignored.”

126. “Duh”

Poor Josh. I love Vincent Rodriguez III’s performance as Rebecca’s idealized man, and he certainly gives each song his all, both as a singer and as a talented dancer. However, for some reason, he just never got that one big song the way the other characters did, and therefore the majority of his pieces will appear lower on the list. “Duh” is the perfect example: the entire premise of the song, set as Josh realizes that he’s meant to be with Rebecca, is just variations on Josh saying “Duh.” It’s a funny and well-written song, but there’s not much more to it than that.

 

125. “Back In Action”

“Back In Action” is a funny moment in the show. It’s a send-up to 80s action movies, specifically Lethal Weapon-esque shows, and it feels appropriately 80s in execution. It also promises a return-to-basics for Rebecca and Paula, two characters who have dramatically grown up during the show, but will always be those insane obsessive stalkers we all know and love (much to Paula’s chagrin). But as a song…it’s a pretty basic metaphor and musical parody. It’s good, and it works in context, but it may be the one you’re most likely to skip when playing your Season Three Best Of playlist.

 

124. “Let Me Be In Your Show”

It’s a little unfair to include any of the Broadway parodies found in Season Four’s “I’m Finding My Bliss.” They’re very short, and they’re intentionally sung poorly by the characters’ real-life voices (one of my favorite aspects of the show is outside of Rebecca’s psyche, these characters are terrible singers). However, these are still good songs, and the tribute to “There’s No Business Like Show Business” is the perfect audition moment for our protagonists. Bonus points for Bloom’s spot-on “Theatre Kid” hands and guest star Cheri Oteri’s note of “Singing…zero. Commitment…A MILLION!”

 

123. “Angry Mad”

Speaking of Vincent Rodriguez III only having simplistic songs that don’t necessarily “pop,” “Angry Mad.” A spot-on spoof of the Footloose warehouse dance, “Angry Mad” is endlessly catchy, and well-danced by Rodriguez. However, there really aren’t any clever lyrics. It’s just Josh Chan shouting “Angry,” “Mad,” and some insertion about his feelings over and over again. Fun to watch, but not really a song that pops off the old iPod when you put Crazy Ex-Girlfriend on shuffle.

122. “Farewell, Fair Mustache”

Pete Gardner’s Darryl is too pure for this world. Originally written as a likable doofus who sometimes says inappropriate things out of genuine naiveté, he’s grown a lot of the years, and given us some of the show’s funniest songs and moments (we’ll get to those). However, his Season Four lullaby, as sung to his recently shaved mustache, doesn’t have the same emphasis as the others. It’s a good song, and the payoff that he isn’t singing to his baby daughter and instead to his iconic character trait is pretty funny, but it’s still just a simple lullaby at the end of the day.

 

121. “The Tick Tock Clock”

Yet another musical theatre spoof from “I’m Finding My Bliss,” “The Tick Tock Clock” is hilariously awful. A spoof of The Pajama Game, the song is basically written as filler to demonstrate the passing of time. The joy here comes not from clever lyrics or musical complexity, but from the childish lyrics – “Tickety tock goes the tick tock clock. Round and round again!” Bonus points for Rachel’s intentionally bad dancing, Scott Michael Foster’s disinterested dancing, and Gabrielle Ruiz’s (the show’s secret weapon) way-too-into-it dancing.

120. “Man Nap”

One of the best “forgettable” songs on the show, “Man Nap” suffers from the early seasons’ dependence on hair rock as a joke. A send-up to Jon Bon Jovi and the “You Give Love A Bad Name” era of rock, “Man Nap” surrounds the general conceit that it isn’t unmanly to take a nap in the middle of the day – and is, in fact, great for physical and mental health. It’s not the most memorable song, but Gardner, Burl Moseley, and Michael McMillan really throw themselves into the performance.

119. “Romantic Moments”

“Romantic Moments” barely qualifies as a song. Set to a romantic, nostalgic R&B beat, the hook of the song is that these are “Romantic moments that he didn’t know were romantic.” It’s a very funny premise, the montage of “ambiguous” scenes is pretty funny, and Nina Zeitlin sings the hell out of it (the way she says “But most likely not” is peak-Bloom comedic sensibilities). But there’s just not enough “there” to put it in the upper echelons of Crazy Ex-Girlfriend songs.

 

118. “Real Life Fighting Is Awkward”

Similar to both “Angry Mad” and “Romantic Moments,” “Real Life Fighting Is Awkward” is a pretty good spoof of “Kung Fu Fighting,” with the imagery of Die Hard, Enter the Dragon, The Karate Kid, and West Side Story. Guest singer Chester Gregory adds a funny layer of funk to the sequence, and the continuous jokes about how fighting is nothing like the movies, with most people hurting themselves and clumsily flailing is increasingly hilarious. But mostly, it’s a filler scene, with gags that mostly only work on a visual level. Still, at least we get the terrific cameo from choreographer Kat Burns.

 

117. “Love’s Not A Game”

Heard in last week’s “I Have a Date Tonight,” “Love’s Not A Game” is significant as the show’s last group number, as well as White Josh’s (David Hull) only lead solo. As a song, it has everything you could want in a Crazy-Ex musical number – it’s a Guys and Dolls spoof (specifically “Luck Be a Lady” and “Sit Down, You’re Rocking The Boat”), it has both Paula and Valencia amping it up, there’s singing cameos from several of your favorite characters (Father Brah! Maya! Hector! Kevin!), and the random Love Bets that the characters place are both in character and oddly hilarious (Josh having the biggest shlong of Rebecca’s love interests and also dying in a parasailing accident are just two of the hilarious jokes in the piece). Still, while I love the premise, both in-episode and in-song, it mostly feels like an attempt to give the gang one last hurrah, and doesn’t quite have the energy of, say, “Friendtopia” or “West Covina.” Solid song, just not one that’s going to see much playtime.

 

116. “What A Rush To Be A Bride”

Some of the best numbers on the show are the duets between Bloom’s Rebecca and Donna Lynne Champlin’s Paula. They have undeniable chemistry, killer singing chops, and an undying dedication to the jokes at hand. A great example of this dynamic is “What A Rush To Be A Bride,” which expresses Rebecca’s overwhelming joy over marrying her beloved Josh, and her celebration with her matron-of-honor. The twist? The song is performed as a death metal screamfest. Listening to Bloom shout back “Love is patient, love is kind!” and her best friend is hilarious and subversive, but once you move past the initial joke, the entire thing is kind of one note. Still, that initial joke is pretty killer.

 

115. “Where Is The Rock?”

“Where Is The Rock?” suffers from being the second hair rock song in a row for the episode “That Text Was Not Meant For Josh!” I’ll be writing more about the wonderful band of lawyers and judges later in this piece (God, I love “Textmergency”), but for now I’ll note that “Where Is The Rock?” is a simple, funny hair song about Rebecca’s carelessness with her scheming and lying eventually catching up with her, as a misplaced rock will give away everything to the naïve and trusting Josh. Especially great is the play on the word “rock” when they note that Josh will figure it out because, “He’s not dumb as a ROCK!”

 

114. “Dear Joshua Felix Chan”

“Dear Joshua Felix Chan” is less a song and more a poem set to music. As Rebecca reads an old love letter she wrote to Josh in the hopes of wooing him, the song works twofold, as a joke and as a sweet moment of earnestness. Yes, Rebecca’s language is overly hyperbolic, and we get why Josh laughs while hearing it. But we also know how Rebecca feels, how she still acts like her 16 year old self, and how everything, from the music to her emphasis, tells us that this is not hyperbole for her. She’s being sincere. So while I mark it down for its brevity and its simplicity, I commend it for its heart. And bonus points for the Trent reprise, “Dear Rebecca Nora Bunch,” which was sadly (or graciously) cut off before it even began.

 

113. “My Sperm Is Healthy”

A cross between techno and “Me Too” by Megan Trainor, “My Sperm Is Healthy exists for two reasons only: one, to give Pete Gardner a much-deserved standout moment, and two, to piss off the censors. Darryl’s ode to the revelation that his sperm count is high enough to produce the second baby he’s always wanted is absolutely joyous, filled with far too much TMI and some expertly-crafted wordplay about fertility. Mrs. Hernandez may think it’s gross, but it’s hard not to love either the infectious beat or the pure joy emanating from Gardner throughout the sequence.

 

112. “Scary Scary Sexy Lady”

“Scary Scary Sexy Lady” is a weird song, even by Crazy Ex-Girlfriend standards. Less a song and more a theme parody to introduce the show’s movie twist, “Scary Scary Sexy Lady” is a comical spoof of Rebecca’s determination to follow in the footsteps of such “heroes” as Alex Forrest from Fatal Attraction, Madison Bell in Swimfan, or Mrs. Mott in The Hand That Rocks The Cradle. It’s a song that almost exclusively works in the context of the episode, which becomes a spoof of sexy psychological thrillers, but it works because of Bloom’s dedication, the perfect guitar riffs, and the delivery of the line, “She’s here to chop your penis off.”

 

111. “How To Clean Up”

The majority of Pete Gardner’s songs on Crazy Ex-Girlfriend have been spoofs of very specific styles of dance/electronic music. “How To Clean Up” is no exception. Designed as a cross between 80s jingles and early-aught instructional dances (like “The Cha-Cha Slide”), the song is simple to the point of being two lines long (“If you see something that’s not where it belongs/Pick it up and put it where it belongs”). However, while it doesn’t make for one of the best songs in the show’s history, the humor of its two-line format does give it a boost in the comedy department.

 

110. “The Math Of Love Quadrangles”

The first of the two exceptions I’ve made for “reprises,” “The Math of Love Quadrangles” isn’t necessarily as funny as its predecessor “The Math of Love Triangles.” So why include it? Two simple reasons. The first is the notion that Rebecca Bunch is miserable having to reprise this song, barely summoning the energy to commit to the bit (her running out only halfway in costume and makeup is pretty great). The second is the way Skylar Astin, Scott Michael Foster, and Vincent Rodriguez commit to the portrayal of the nerdy background dancers. One of the funniest moments is when they stare into the camera and declare, “Joke’s on you, bitch, you’ll never be free!” Not quite enough to make it one of the most memorable (especially not with the near-perfect original in the mix), but still enough to warrant its placement on the list.

 

109. “Nothing Is Ever Anyone’s Fault”

Scott Michael Foster’s “Nothing Is Ever Anyone’s Fault” is funnier in concept than in execution. Inspired by the song “All The Wasted Time” from the 1998 musical Parade, the song operates under a simple premise that slowly grows more and more grandiose (the recipe to any great Crazy Ex song): that Rebecca has taught Nathaniel a valuable lesson about responsibility – namely, that everything in life, especially the bad things we do, are in fact because of genetics and bad parents. The song isn’t as great as, say, “You Stupid Bitch” or “Strip Away My Conscience,” but I dare you to listen to Foster’s performance and not think this is a masterpiece. After all, the Big Bang was the original bad father, and it technically wasn’t Hitler’s fault.

 

108. “Ping Pong Girl”

As noted above, most of Vincent Rodriguez III’s songs qualify as “filler.” However, just because these songs don’t have the same impact as, say, “What’ll It Be?” or “Textmergency,” it doesn’t mean that he doesn’t sell the hell out of them. For proof, look no further than “Ping Pong Girl,” the show’s send-up to Bowling For Soup, Blink-182, and LEN. A power pop anthem about how Rebecca’s prowess at ping pong will make her desirable by making her awesome without threatening men’s masculinity, Rodriguez does manage to get some solid zingers into the rather straightforward song, like, “Whoa! She scored 1000 points! I think I love her!” and “She is so indifferent! It makes me want a tangible commitment!”

 

107. “Clean Up On Aisle Four”

Hey! Did you remember that there’s a subplot in Season 1 where a grocery clerk named Marty tried to woo a Rebecca stand-in away from Grocery Clerk With Half An Eyelid? No? Well, that’s not surprising, as it was a random one-off four years ago. But it is a little sad, because it means you’ve forgotten the hilariously awful twee love song that Hunter Stiebel sings (with help from Greg Serrano, who we are absolutely getting to) to the “love of his life.” Featuring hilariously bad grocery puns, including the cackle-worthy, “I’m the pimento to your olive/I want to be inside of you,” “Clean Up On Aisle Four is forgettable and short, but oh so good in the moment – sort of like the pretzels that Rebecca so desperately loves.

 

106. “Forget It”

It feels like blasphemy to put any Tovah Feldshuh/Naomi Bunch songs below the halfway mark, because her character is so integral to the show, and Feldshuh plays it so well. However, as dedicated as Feldshuh is to “Forget It,” and as catchy as the song is, it doesn’t have the same emotional resonance as some of her greater moments. A parody of the Diva Song (think Madonna or Nicki Minaj), the song features Naomi’s attempts to shame her daughter into following the path she’d laid out for her. In her efforts, she invokes the notion that everyone in the neighborhood, especially the frame maker, would judge her and ruin her life. While the song isn’t as impactful as Naomi’s songs in the first two seasons, there are a few great lines, though, specifically, “In your search for happiness, you’ve never thought of me.” And the payoff where Naomi is joined by a chorus of judgmental moms, including Hindu, Italian, African, and WASP (“Everyting’s fine, dear”) is entertaining.

 

105. “We Should Definitely Not Have Sex Right Now”

“We Should Definitely Not Have Sex Right Now” is the perfect example of the Crazy Ex-Girlfriend formula, especially in the early seasons. Utilizing sexy Kenny G sax and some lustful R&B, the song explores the moments in relationships where couples put off arguments and scary subjects by having sex, even though they know they shouldn’t. The song’s humorous evolution evolves from “We shouldn’t have sex right now” to “It’s so good to be having sex right now” to “We can’t stop having sex right now” and finally back full circle to “We should definitely not have sex again.” There’s not much more to the song than that premise, and the music is a little simple in nature, but as a whole, it still works just fine.

 

104. “Slow Motion”

Similar to “We Should Definitely Not Have Sex Right Now,” “Slow Motion” parodies the use of slow motion in movies when a group of hot, badass women walk into a room dramatically. The sequence has two main jokes. The first is that the characters narrate the sequence, through every movement, from sneezes to hair flips to giving directions to the mistake of trying to actually walk in slow motion as opposed to adding it in post. The second are the tricks the camera plays, as they ask it to slow down for them, freeze, and eventually go “even slower,” which turns out to be a huge mistake. It’s a pretty simple joke, but that doesn’t make it any less fun to watch! Bonus points for Valencia shouting “Slay!” which is by far my favorite moment.

 

103. “Period Sex”

Perhaps the most hilariously disturbing song on the list (for most of Season Two, no character would let Rebecca actually sing it, always cutting her off mid-chorus), “Period Sex” gets onto the list as a technicality. As mentioned, it was never heard in its entirety until the soundtrack. That being said, the full version of this song is too good to pass up. Deemed “too graphic” for TV, the song features a series of detailed quips by Bloom (I won’t even pretend this is Rebecca Bunch) about the art and joy of having sex while the woman is on her period. As the song goes on, it goes from the mildly vulgar (“Put down a towel and party till its dry!”) to the gross (“Think of it as Mother Nature’s juice cleanse!”) The payoff of, “Were those sheets expensive?” gives this song the extra boost, even though its Internet-Only existence dooms it to the lower half of the list.

 

102. “If You Ever Need A Favor In Fifty Years”

I place the camp song parody “If You Ever Need A Favor In Fifty Years” lower on the list because I found it a simpler, less effective song from the impressive fourth season. That being said, I fully admit that the reason this song didn’t quite land with me may be because it wasn’t for me. I get the feeling that the “Camp Kavetcha” anthem, as sung by Naomi Bunch and actual comedian Elayne Boosler, is written about a certain type and age of Jewish woman, and written for that certain type and age of Jewish woman. As I am neither of those things, I’m a little bit on the outside. Still, I can appreciate a few of these jokes, including the massive amounts of hording inside their prada bags, or the way the lyrics are eerily pertinent to the very situation the women are in at this very moment, or even that the final lyric is talking about how the girls in the camp all have dads who are dentists, bankers, and so on. It’s a very particular song for a very particular type of person, and while it wasn’t for me, I give it props for taking that risk.

 

101. “Makey Makeover”

The show’s tribute to “Mickey” by Toni Basil, complete with Bloom in a Bring It On-esque cheerleading outfit, isn’t necessarily that clever – it’s just her baby-talking a series of variations on the phrase “Makeover.” However, the song’s incessant commitment, Bloom’s pronunciation, and the final twist of “I had a stroke!” gives the simple ditty a distinct edge.

 

100. “You Go First”

“You Go First” is the perfect example of a fine song elevated by the performances of Donna Lynne Champlin and Rachel Bloom. Set around the pettiness of two friends in a fight who want to make up, but need the other person to apologize first, the music parodies everything from Heart’s “Alone” to Ozzy Osbourne and Lita Ford’s hair-metal “Close My Eyes Forever.” The lyrics have an overwhelming sense of longing, and the childish “But you go first” mixed with the confession that “This is almost entirely my fault, but you gotta admit it’s a tiny bit your fault too!” is just straight comedy. Still, it’s hard to shake the feeling that this song has just fallen by the wayside in the face of other great duets and quartets in the show’s run, thus knocking “You Go First” down a few pegs.

 

99. “You’re My Best Friend (And I Know I’m Not Yours)”

Pete Gardner’s best moments on Crazy Ex-Girlfriend came when he doubled down on the sensitivity of the character through loving odes. One of his sweetest moments was his Jason Mraz send-up to Paula, “You’re My Best Friend (And I Know I’m Not Yours).” The song tackles the awkward situation where one person considers someone their best friend, while the other person doesn’t reciprocate. While such a situation can put a strain on a relationship, Darryl doesn’t let it bother him – he instead relishes in knowing he can be there for someone. As he puts it in the song, “And that’s ok!”

 

98. “After Everything You Made Me Do (That You Didn’t Ask For)”

And now it’s time for our second of four reprises that managed to sneak their way onto this list, “After Everything You Made Me Do (That You Didn’t Ask For).” Bloom’s rendition of Champlin’s crowning achievement (you bet your sweet ass we’ll be talking about that in the Top 20) isn’t quite the same in terms of its emotional “Rose’s Turn”-esque delivery. However, the song makes the list thanks to its in-show contexuality, as well as its fiery performance. Set as Rebecca begins her shame spiral that eventually leads to a suicide attempt, the sequence features her emotionally and angrily revealing every bad thing she’s done on the show to her ex-fiancé Josh Chan. It both lays everything bare amongst the characters and eliminates any secrets they may have, as well as allows Bloom a chance to wholeheartedly demonstrate the mental state of a woman coming undone. Both hard to watch and wholly fascinating, “Everything You Made Me Do” is a worthwhile reprise.

 

97. “Get Your Ass Out Of My House”

“Get Your Ass Out Of My House” is not my favorite song, for a litany of reasons. It’s karaoke format is a little on the nose, and the critique of grown men still living with their parents tries to walk the fine line (mostly successfully) between cruel and tough love. Still, Amy Hill sings the hell out of the song, and some of the jokes about the things parents want to do after their children finally leave are pretty humorous. I give it credit for Hill’s performance, which is for sure worth a watch.

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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