Greatest Hits: A Crazy Ex-Girlfriend Retrospective

Nothing makes me laugh more than a silly song. The relationship between comedy and music has always been my favorite one, and the one that has defined my life more than any other.

My favorite piece of media ever filmed is Dr. Horrible’s Sing-Along Blog, the 2008 musical superhero mini-movie written and directed by Joss Whedon. I rewatch it at least three times a year.

My favorite movie ever is John Carney’s 2016 masterpiece Sing Street. It’s a comedy about a kid in Ireland in the 1980s who starts a band. I listen to the soundtrack all the time and rewatch the movie once or twice a year.

If someone asked me what the greatest song ever written was, I’d probably tell them it’s “Issues (Think About It)” by Flight of the Conchords. If someone asked me who my childhood heroes were, I’d tell them Andy, Jorma and Akiva from The Lonely Island. The comedy special I think about more than any other is Bo Burnham’s Make Happy, a melancholy blend of comedy, performance art, therapy and music. 

In the 2010s, Crazy Ex-Girlfriend earwormed its way into my soul. 

This decade was full of sitcoms that changed my perception of the world. But I don’t think there was another show that challenged my belief system and understanding of humanity like Crazy Ex-Girlfriend did. Not just in the way that it made me more compassionate and understanding, but also in the way that it taught me truths about myself that I didn’t yet know.

But enough about the sappy stuff. Let’s talk about songs.

Ranking all the 130 or so songs in the Crazy Ex-Girlfriend catalogue would take too long. (And I’m pretty sure Vulture already did it.) So I’ve decided to pick 20 CXG songs and make my version of a greatest hits record.

Keep in mind, these aren’t necessarily my 20 favorite songs. And they’re definitely not 20 songs that tell the story of the show. I’ve just picked 20 songs (five from each season) that I think do a good job of showcasing the talents and strengths of this wonderful, wonderful show. 

Some of them are heartfelt. Some of them are plot-heavy. Some of them are parodies. But they all work. And all of them have incredible laugh-out-loud moments that still make me giggle after dozens of listens. 

So here it is. A Crazy Ex-Girlfriend Greatest Hits Album, listed chronologically based on when they aired:

Track 1: Feeling Kinda Naughty (Season 1, Episode 2)

Whenever I try to explain the sense of humor of this show to anyone, this is where I start. Parodying I Kissed A Girl in 2015 should’ve already been well-tried territory. But Rachel Bloom pulls it off with deeply disturbing lyrics that all my poor friends recoil at when I play this for them because they never see it coming.

Locking a girl in your basement. Stealing her baby teeth. Taking measurements of her body so a surgeon can transform you into her clone. All in the name of “feeling kinda naughty.” If the two songs in the pilot (West Covina and The Sexy Getting Ready Song) were a thesis statement about the topics and themes the show would attack, Feeling Kinda Naughty is the proof that comedy wouldn’t get in the way of those themes. They can coexist. And they did.

Track 2: Settle For Me (Season 1, Episode 4)

Settle For Me is a difficult song to write about for me. I’m attracted to this one for the jokes. And with lines like “If he’s your broken condom, I’m Plan B,” Settle For Me might contain the best wordplay of any song in the show.

But I also think of this song as one of the most manipulative in the show. I’m not #TeamGreg (more on why later), so when I hear him singing about how Rebecca should lower her expectations to settle for him, I feel genuine frustration. First off, don’t tell her what to do. Second off, don’t expect everyone else to conform to your expectations.

I think I feel so much frustration with this song because some of my least proud moments have come when I thought like Greg. I can relate to his character for all the wrong reasons.

That shame is another reason why I get so much pleasure out of this song, though. Settle For Me packs itself with jokes, but also with a deeper twinge of awareness of the selfishness that comes with trying to make someone fall in love with you.

Track 3: What’ll It Be (Season 1, Episode 6)

After three paragraphs of ritualistically shaming Greg, now I’m back on his side. Because What’ll It Be — Crazy Ex-Girlfriend’s pitch perfect parody of Piano Man — is a remarkable achievement. 

At its core, Piano Man is a song about arrogance. The whole ‘Man, what are you doing here?’ vibe of the song reeks of ego. And Greg’s ego takes centerstage in this one. But this time, we sympathize with Greg’s ego. He feels trapped. He wants to leave but he can’t. He’s unhappy and he feels like there’s no way out of it. 

Santino Fontana’s performance is magnificent. He’s smug. He’s smarmy. He’s all sorts of arrogant. But he’s also pitiable and soft and you can’t help but yearn along with him. This song rules.

Track 4: You Stupid Bitch (Season 1, Episode 11)

You Stupid Bitch is probably the most painful song in the series. Rebecca’s self-indulgent self-loathing marks the turning point in the series (along with “The Villain In My Own Story,” which comes four episodes later). This song is when it becomes evident that Rebecca’s actions will have repercussions, and that Rebecca’s move to West Covina wasn’t as whimsical as it might’ve first appeared to be.  

It still pains me so much to hear Rebecca smile through the line “Yeah, you guys know this one” at the top of the song. She’s singing about shaming herself into a spiral of self defeat. She’s singing about the weight of her actions feeling like being crushed by a boulder. She calls herself a bitch and a slut and horrible and stupid and dumb and ugly and fat and simple. And the worst part is when she says she deserves all of it.

It’s a song about self-hate, a feeling I think we’re all ashamed to say we can relate to. But Crazy Ex-Girlfriend made such an artful and compelling ode to this feeling. And it’s the song that turned this show for me from something I mindlessly enjoyed into something I was deeply invested in.

Track 5: Oh My God I Think I Like You (Season 1, Episode 17)

It’s nearly impossible for me to choose just one song from this episode. I Gave You A UTI might be the pound-for-pound most joyful song in the show. But ultimately, I’m gonna pick Oh My God I Think I Like You. And not just because it reeks of influence from my girl Carly Rae Jepsen. Also because this song reeks of the tone Rachel Bloom thrived on before Crazy Ex-Girlfriend was ever a thing.

The sweet, bubblegum vibe of the song juxtaposed against the raunchy, oversexualized lyrics are funny. But Crazy Ex-Girlfriend already traversed that territory with the aforementioned Feeling Kinda Naughty. What this song adds is heart. It’s both sweet and tragic when you hear a lyric like “But as my body’s getting ruined, like, really trashed, I only wanna look in your eyes.” 

Then there’s the bridge. “Are there condoms that can prevent these feelings? Is there spermicidal lubricant that can kill the fluttering in my heart? Is there an IDU that can stop the image of you and me getting married on a hillside surrounded by ducks and then we get into the rowboat… Oh My God I Think I Like You.”

I don’t talk much (or enough) about acting or direction. I mostly focus on the songs and lyrics. But Rachel’s performance on that last line as she’s having her head pushed down the front of a fridge but conveys all that meaning in her eyes? Man, that’s just great. Great for comedy and great for, to quote this song, the feels.

Track 6: The Math of Love Triangles (Season 2, Episode 3)

This song says nothing about the show and it doesn’t need to. The Math of Love Triangles is a spot-on parody of Marilyn Monroe with the most surprising and genuinely impressive vocal performance Rachel Bloom pulls off in the show. 

It’s three minutes of sex jokes and triangle puns. There’s not much else I can add. It’s a masterpiece of songwriting and set designing and choreography and testing the limits of my memory of my 10th grade trigonometry lessons. This song was as funny on Crazy Ex-Girlfriend as it would’ve been on SNL or as a Robin Sparkles bit in How I Met Your Mother. It’s just a straight-up funny song. No need to overthink it.

Track 7: We Tapped That Ass (Season 2, Episode 4)

When it comes to songs that bang, the first half of Season 2 feels like Crazy Ex-Girlfriend’s peak. This most evident in the first 20 minutes of Season 2, Episode 4 when we get Greg’s heart-wrenching goodbye song “It Was a Shit Show,” followed closely by Josh and Greg going all dream-ghost-adjacent with We Tapped That Ass.

It’s pretty clear at this point that my musical theater knowledge isn’t all that extensive. Nor is my knowledge of classic musical cinema. But even I got this reference. And I laughed my way through it. It’s crass. Sometimes the humor borders on immature. But it also radiates joy in a way only a song performed by Santino Fontana and Vinny Rodriguez could. 

The wordplay is fresh. The dancing is mesmerizing. And there’s an underlying hint of self-loathing reminiscent of You Stupid Bitch layered throughout the song since Rebecca is the one imagining this whole thing. It’s a phenomenal song, and a fitting farewell for Greg. For now.

Track 8: You Go First (Season 2, Episode 7)

If I’m ranking my personal favorite songs in the series, this is probably in second place. You Go First is an obvious parody of 80s female power ballads by acts like Heart and Bonnie Tyler. And it just works so, so well. 

You Go First might be the most passive aggressive song ever written. Performing an entire song about wanting to reconcile with your friend, but only after she reconciles with you is a masterstroke of making fun of how dumb the human condition really is. The whole bit about rehearsing an “Oh, no no no, please” response to an apology feels way too real. 

Then there are the billowing curtains. The ever-growing mullets. The acrobatic dancer straight out of an Olivia Newton-John video. Paula’s dope-ass leg kick. This is the most aesthetically hilarious song in the series, and it’s a song that I think might read as funny to people who haven’t even seen the show. It just works. 

Track 9: Santa Ana Winds (Season 2, Episode 11)

It’s hard to call this one song. Santa Ana Winds is a running gag throughout an entire episode that you can composite into one song. And if you do, you get one of the best bits in the whole show. 

A Jersey Boys spoof about a natural phenomenon native to the west coast is too specific of a joke. It shouldn’t work. But it does. It works really, really well. Pair in some science jargon reminiscent of the math puns in Triangles and a harrowing throwback to You Stupid Bitch and you get yourself an earwormy pop song that also reveals so much about Rebecca and the self-defeat that she’s layering on top of her self-hatred. 

Track 10: Let’s Have Intercourse (Season 2, Episode 11)

Two songs from the same episode? That must be a darn good episode. (It is.) 

Let’s Have Intercourse has ruined Ed Sheeran for me. Not just Thinking Out Loud. But all of Ed Sheeran’s work. This song is such an eviscerating takedown of Sheeran’s vibe that I can’t listen to his music anymore. (Fine, Castle On The Hill is ok.)

Every joke in this song lands. From the bit about Nathaniel acknowledging Rebecca’s intellect and demeaning her appearance in the same sentence to “you could use the exercise” to rhyming unfortunate with “contortion it” to wondering about nipples. All the jokes land. What an introduction for Scott Michael Foster as the best comedic force in the show’s later seasons.

Track 11: Let’s Generalize About Men (Season 3, Episode 1)

I don’t like using terms as prosaic and oversimplified as “best” or “favorite.” (Says the guy who devoted six months of his life to ranking the 50 best sitcom episodes of the 2010s.) But yeah. Let’s Generalize About Men. It’s the best. It’s my favorite. No questions.

It’s bright. It’s colorful. It’s dripping with hairspray and irony. In the live concert retrospective for the series, Rachel Bloom described this song as simultaneously feminist and anti-feminist. It reminds me a lot of TGS Hates Women, the episode of 30 Rock where Cristin Milioti guest stars as an over-sexualized Barbie doll of a woman who Liz tries to change, but unwittingly reveals her disguise and exposes her to a stalker. It’s well meaning in all the wrong ways

Let’s Generalize About Men also has some of my favorite vocal performances in the series. Especially Vella Lovell. She just feels like she belongs in a Pointer Sisters or Weather Girls song. Not to mention Gabrielle Ruiz’s growly growl. It’s just so damn perfect.

Track 12: I Go To The Zoo (Season 3, Episode 3)

Confession time: I’m #TeamNathaniel. Reformed frat bro with a conscience is such a phenomenally specific and poignant trope to lean on, and the show did it so well. Especially in Season 4. But you can see the seeds of it in Season 3, especially with this song where he drops the hardened facade and sings about his love for fishies and cheetahs and kangaroos and monkeys whose eyes look like his.

Based on the colors and beat, this song is probably a spoof of Hotline Bling. But it always felt to me like a takeoff on musicians like Jason Derulo and Flo Rida, guys who constantly brag about the money and women and parties they’re around. It comments on the emptiness of the over-commercialized pop and hip hop industries much in the same way that Lorde’s Royals did a few years before. With a few built in jokes about bottle-feeding panda cubs.

Track 13: A Diagnosis (Season 3, Episode 6)

In a lot of ways, I think Season 3, Episode 6 is a second pilot for Crazy Ex-Girlfriend. Two episodes before, with “Josh’s Ex-Girlfriend Is Crazy,” the arc of the first two seasons ended. The following episode, “I Never Want To See Josh Again,” functions as an interlude as the characters cope with denial. Then the show reboots itself with “Josh Is Irrelevant.”

If we’re assuming Josh Is Irrelevant is a second pilot, then A Diagnosis serves the function that West Covina did in the original pilot. Rebecca’s got a new plan for how to feel better, a new lavish musical theater number to explain it and a new iconic dress to mark her mood. (Is it a coincidence that the dress in West Covina is blue, the color of depression, and the dress in A Diagnosis is yellow, the color of the sun? Probably not.) The only difference? West Covina was about finding validation in others. A Diagnosis marks the beginning of Rebecca’s difficult and complicated journey to self-discovery.

Sure, this song has jokes. The bit about hearing voices makes me chuckle, and the jab at naturopathic medicine is funny. But this song is more than jokes. It’s a fresh start. It’s a new lease on a show that got incredibly dark so that the sun could rise again. It’s such an important song for the series, and it’s one that gives me hope.

Track 14: Without Love, You Can Save The World (Season 3, Episode 9)

Full disclosure: Without Love, You Can Save The World came out a whopping three days after the beginning of a hard breakup that took me about two months to get over. So I leaned on this song pretty hard when it first dropped, and I’ll always have some sentimental connection to it because of that.

But also, this song is just really clever. “Forget who you did, think about what you can do” is such an awesome thesis statement. The entire cast rocks it in this song. And I still have major beef with the Spotify version of this song not including the best line: It’s an asexual utopia! 

Honestly, I love a good full-cast song. I think this is the first one I’ve included so far. But as the show neared its end, it added in a few great full-cast ditties. Can’t wait to talk about all those.

Track 15: Nothing Is Ever Anyone’s Fault (Season 3, Episode 13)

Picking a fifth song from Season 3 was probably the hardest choice for this list. I probably should’ve gone with The End of the Movie from Josh’s Ex-Girlfriend Is Crazy. But in my last album binge before I started writing this, I rediscovered this gem from the Season 3 finale.

Nothing Is Ever Anyone’s Fault is one of the simpler, more straightforward songs in the series. It’s about denial. Rebecca and Nathaniel are denying culpability for any of the bad things they’ve ever done because they have traumatic backstories. In five words: Psychology is a great excuse. 

Is the Hitler bit a little overused? Maybe. But calling the big bang the ultimate bad father and blaming it for the entirety of human suffering is a darn-near perfect way to lampoon delusion. There were funnier songs in Season 3 I could’ve picked (The Moment Is Me, Buttload of Cats, etc.). And there were more ambitious and catchy songs (First Penis I Saw, This Session Is Gonna Be Different, etc.). But this song is a perfect ending to the complicated and powerful third season of this complicated and powerful show.

Track 16: No One Else Is Singing My Song (Season 4, Episode 1)

Another personal connection: This episode and song debuted on a day where I moved to a new city where I didn’t know anyone. For the second time in four months. I was stressed. I was scared. I was lonely. This song almost made it better.

There’s a website called The Dictionary Of Obscure Sorrows that aims to make new words and definitions for feelings that we all have but don’t have words for. (I learned about it through a YouTube review of an episode of Buffy The Vampire Slayer. Yay, television!) One of those words is “sonder,” which the DOOS defines as “the realization that each random passerby is living a life as vivid and complex as your own.” 

This song, bitingly sarcastic as it may be, led to me accepting the truth of sonder. If you ever feel alone, scared, beaten or tired, it’s easy to sing this tune. It often feels like we’re the only people going through our sorrows. But we obviously aren’t. Everyone is experiencing something.

That’s the beauty of this song. “Maybe while I’m singing my song, someone else is singing along.” That’s it. That’s the whole value of this song. It makes me feel all the right emotions.

Track 17: Don’t Be A Lawyer (Season 4, Episode 3)

Now for something completely different.

Heading into Crazy Ex-Girlfriend’s fourth season, I was afraid the show had ran out of genres to parody. Then I heard Don’t Be A Lawyer and realized I was so, so wrong. This pastiche of every new jack swing cliche is one of the better genre parodies the show ever did. And unlike songs like Settle For Me or You Go First, Don’t Be A Lawyer comes from a genre that isn’t often parodied. So all the vocal and choreographic cliches being pointed out seemed like original jokes rather than retreads.

The bow on the whole song is the great line where Jim sings “there are so many other professions that won’t turn you into Jeff Sessions.” This show rarely went topical or political, but when it did the jokes landed hard. Even if that line won’t age super well, in 2018 it was perfect.

Track 18: Trapped In A Car With Someone You Don’t Want To Be Trapped In A Car With (Season 4, Episode 6)

By sheer coincidence, I think I’ve picked almost all of the songs with the longest titles in the show. Weird.

Anyway. Of course I’m going to pick the never-ending song that manages to parody three different phases of the Beach Boys’ career in one ever-shifting song. They nail the Fun, Fun Fun era. They nail the Pet Sounds era. And they absolutely slay the Kokomo era. 

The lighting, sets, dancing, vocal harmonies and barking-dog sound effects were all on point. And using the Beach Boys as the backdrop for a road trip song is just meta in all the right ways. The first (indescribable) instant I heard this song, I knew I’d love it. And I was right.

Track 19: I Hate Everything But You (Season 4, Episode 12)

I’ll be brief with this explanation. Skylar Astin rocks doing a Bruce Springsteen impression. Instead of explaining why this song is good, here’s just a list of all the words in the song that make me laugh when they’re growled in a Bruce voice:

Hour, bling, everything, shampoo, “the wave,” Caddyshack, true, done.

Track 20: Love’s Not A Game (Season 4, Episode 16)

The last completely original song in the series is also the best ensemble number in the show. Everyone gets a moment, from Mrs. Hernandez to Sunil to Jim and Tim and George and our beloved Father Brah. And every joke works. 

It’s a little weird to me that most of the jokes come at the expense of Josh, positive ones and negative ones. But that’s a small gripe for a song that otherwise rules. The colors alone are enough to entrap you like a siren’s call. But then you look closer and see the inside jokes scribbled on the betting boards. And you notice the irony of WhiJo leading the callback to Group Mind. 

I like Eleven O’Clock. It was a fitting and proper send off for a show I obviously love. But this was the real goodbye song for me. It’s fun. It’s vibrant. It’s funny. It’s biting. And it sums up just about everything I love about musical comedy. Like Crazy Ex-Girlfriend as a whole, I guess.