Crazy Ex-Girlfriend was an overlooked masterpiece

Imagine what a tough sell Crazy Ex-Girlfriend must’ve been when creators Rachel Bloom and Aline Brosh McKenna were first shopping it around Hollywood.

It’s hard to sum up the essence of the show in a succinct soundbite. The shortest elevator pitch goes something like this: Check out this wacky romantic comedy that stars a woman who tries to find happiness by fixating on love and also views her life as a musical and is also suffering from a severe undiagnosed case of borderline personality disorder!

That doesn’t exactly roll off the tongue. Most importantly, it doesn’t do any justice to a quirky, wonderful show with killer original music and a real understanding of its characters that was unafraid to constantly reinvent itself. Two years later, at the end of the show’s impressive four-season run, Crazy Ex-Girlfriend has earned the right to be remembered as an overlooked masterpiece of the prestige TV era.

Like most of the last decade’s best TV comedies, Crazy Ex-Girlfriend was both hilarious and startlingly dramatic at times. One minute, Rebecca Bunch (creator, writer and star Bloom)  is singing about how maybe her overbearing mother wasn’t such a heinous bitch after all. A few scenes later, she’s washing down a bottle of pills with some Merlot on a cross-country flight. The show’s ability to tap into your funny bone and tear ducts in equal measure was extraordinary for a network series.

Striking that balance wasn’t smooth sailing for Crazy Ex-Girlfriend. Bloom and McKenna (who also wrote The Devil Wears Prada) were originally developing a half-hour Showtime original series. When Showtime passed, The CW stepped in and helped Bloom and McKenna re-imagine Crazy Ex-Girlfriend as an hour-long affair.

Crazy Ex-Girlfriend fit The CW’s aesthetic, but not its tone. It was approximately a billion times more zany than anything else the network had to offer, and also way more raunchy. For proof, check out the dirty version of “I’m So Good at Yoga.” And let’s not forget this is the show that somehow got away with using the phrase “let me choke on your cocksuredness” in the song “Strip Away My Conscience.”

Unsurprisingly, the show didn’t find its legs and decide what it wanted to be (a.k.a. everything) until a few episodes into its first season. It also had to deal with a few significant cast reshuffles over its four seasons. Chiefly, there was the departure of the great Santino Fontana, the introduction of Scott Michael Foster’s Nathaniel and the return of Fontana’s character, Greg, recast as Pitch Perfect star Skylar Astin. That’s a precarious position for any form of entertainment that relies on finding an audience for survival.

It’s also worth mentioning that the name itself created a barrier to entry. Crazy Ex-Girlfriend was probably meant to be a cheeky dig about how society labels strong-willed women as “crazy” and a nod to Rebecca’s mental-health struggles. But it’s also easy to see how one could consider it weird and alienating.

And yet, the little show that could persisted. It attracted a big enough audience to warrant a few more seasons and only gained steam creatively. It even earned a big enough fanbase to support  a country-wide concert tour featuring its cast singing the show’s signature numbers.

So, how did this strange, unprecedented, raunchy show with a seemingly dumb name from an unproven star-creator that faced behind-the-scenes obstacles from the beginning and a not insignificant amount of cast upheaval become the hilarious, honest, lovable show it did?

The answer, friends: by proving its mastery in casting, musical comedy and world-building that allowed it to rise to the occasion every time.

When TV historians try to determine what made Crazy Ex-Girlfriend as good as it was, the first thing they’ll discuss is the fact it proved that a TV musical can, in fact, actually work. Eat your heart out, Glee.

Think about the degree of difficulty involved in every Crazy Ex-Girlfriend episode. Not only do they each have to fill an hour of CW airtime minus commercials, but they also contained one-to-three original songs. Basically, the show was putting out at least one intricately filmed music video per week. Now that’s crazy.

The best Crazy Ex-Girlfriend songs tend to follow a similar formula. Those numbers are generally hilarious, parody a specific musical genre, have something to say about the world at large and often reveal something about a character the audience hadn’t quite realized.

The best example is season 2’s “The Math of Love Triangles,” which allowed Rebecca to work out her romantic dilemma while lampooning both classic movie-musical numbers and songs where women dumb themselves down. It even finds time for some great sex and math puns.

Sometimes a song wasn’t that deep but was just plain hilarious, like another season 2 standout, “We Tapped That Ass.” In this one, an imaginary Greg (Santino Fontano) and Josh (Vincent Rodriguez III) paid tribute to “Singin’ In The Rain” by cracking tap-dancing jokes about all the places they had sex with Rebecca in her house. It somehow found a rhyme for the word ottoman, a feat that would make a genius like Lin-Manuel Miranda proud.

Crazy Ex-Girlfriend inadvertently put out a song that seemed designed for the #MeToo era with season 3’s “Let’s Generalize About Men,” which is exactly what its four female vocalists do. It came out right around the time the Harvey Weinstein scandal broke and, as Sonia Saraiya astutely put it in Variety, provided “a welcome antidote of upbeat, thoughtful sass — one that lets you feel the complexity of a situation and enjoy it anyway.”

At other times, the show’s musical numbers were squarely focused on Rebecca’s journey to emotional stability. From a La La Land parody about how anti-depressants aren’t a big deal to an anthem about Rebecca finally getting a concrete diagnosis for her condition, Crazy Ex-Girlfriend was never afraid to incorporate its heavier themes into its music.

And then there are the moments where Bloom took advantage of her role as creator to cater to the female gaze. Look no further than a strip-tease song called “Fit Hot Guys Have Problems Too.” Enough said.

What do these songs all have in common? They’re really, really good! Not every Crazy Ex-Girlfriend musical moment was a hit like these, but none were bad. That’s a huge achievement for a show that relied so much on this particular gimmick.

In addition to its strong music, Crazy Ex-Girlfriend was also particularly adept at writing well-thought-out characters and casting actors who could really capture what makes them tick.

Crazy Ex-Girlfriend was a low-key great example of television world-building. It didn’t invent an entirely new world a la Game of Thrones, but West Covina always felt like a vibrant, well-defined setting with a recurring rotation of silly characters. The show’s ability to populate its universe with a revolving door of people who fit its specific tone was downright Simpsons-esque.

That also speaks to the show’s deep understanding of everyone in its orbit, from its main cast down to the supporting players. The best example of that was, of course, just how well-written and acted its protagonist, Rebecca Bunch, was. For evidence of her growth from premiere to finale, just examine Crazy Ex-Girlfriend’s four theme songs.

Rebecca was originally positioned as a depressed New York lawyer who was given a new lease on life when she randomly ran into her old camp crush, Josh Chan. She may have followed him to California, but as the season 1 theme song spelled out, “The situation’s a lot more nuanced than that.”

It quickly became clear that Rebecca had some unresolved issues related to her desperation to win Josh’s heart. We eventually learned more about her fraught relationships with both her parents and past significant others. The audience even began to see that she had a strange concept of the role love could play in unlocking her ultimate happiness.

As the season 2 theme song laid out, she was just a girl in love. If love makes you crazy, how can you hold her accountable for her frequently erratic behavior?

The show finally dove head-first into her core problems and what it really means to be “crazy” in season 3. The theme song for that season is one of the show’s crowning musical achievements. It manages to skewer four musical genres at once while cutting to the core of Rebecca’s constant mental-health struggles.

Once she morally and legally took responsibility for her actions at the end of season 3, Rebecca began to rebuild her life into what she’s always wanted it to be. As the season 4 theme song explained, she had evolved so much from the wide-eyed love addict we were introduced to in season 1 that she’s now “too hard to summarize.”

That’s the arc of a fully realized character whose story probably resonates with many out there dealing with similar issues. Bloom’s performance has always sold both Rebecca’s pain and her intense desire to find her bliss. She’s not exactly Julia Louis-Dreyfus on Veep, but hopefully the Emmys will give her a career-achievement nomination for four seasons of incredible triple-threat work.

Then there’s the rest of the cast, whose demons Crazy Ex-Girlfriend made a point to unpack almost as much as Rebecca’s. From Paula (Donna Lynne Champlin) gaining the confidence to pursue a law degree, to Heather (Vella Lovell) realizing she can’t be a student forever, to embracing what a lost man-child Josh actually was all along, the show paid the right amount of attention to all its characters’ lives.

It also did a stellar job crafting a love quadrangle with three suitors who all have a legitimate shot at Rebecca’s heart. Nathaniel went from being a jerk to a sincerely nice guy, both versions of Greg worked through his alcohol addiction to become a less miserable person and Josh has proven at least to be a sweet and loyal companion.

Crazy Ex-Girlfriend even turned out to be exceptional at taking unlikable characters and making you root for them, the main examples of which are Nathaniel and Valencia Perez (Gabrielle Ruiz).

Valencia in particular is a case study in how to turn a villain into a hero. Originally conceived as Rebecca’s main competitor for Josh’s affections, the two eventually became friends and Valencia was allowed to grow into a confident, sexually fluid career woman. Plus, it turned out Ruiz was really funny to the point that Valencia is easily the show’s secret weapon. That’s some Jaime Lannister-esque character rehabilitation.

It’s also remarkable that Crazy Ex-Girlfriend seamlessly transitioned away from a major character early in its run, introduced a new one perfectly tuned to the show’s rhythm and then went back to that original character but with a different actor.

The Greg situation completely changed the DNA of the show and then somehow still worked even with a new actor. Greg first appeared in the pilot as one of Josh’s West Covina buddies who Rebecca used to get closer to Josh. She eventually realized the two of them had a connection that may have made more sense than Rebecca continuing to pursue the then-unavailable Josh. Greg even once begged Rebecca to settle for him, admittedly not one of his proudest moments.

Fontana played Greg as an eternal grump who turned to misplaced anger and alcohol to cope with his dissatisfaction at his lot in life. He pulled off a tough balancing act where viewers could rightfully be annoyed with Greg’s behavior but still root for him to get better and figure it out with Rebecca.

It didn’t hurt that Fontana may have had the best voice of anyone on the show outside of Champlin. One of the funniest songs in Crazy Ex-Girlfriend history was “I Gave You A UTI,” a Greg solo number about how proud he was about doing just that to Rebecca and how that’s not an impressive accomplishment. He wrings every bit of humor out of Greg’s misdirected hubris.

When Fontana exited Crazy Ex-Girlfriend a few episodes into season 2, it was unclear how the show would cope going forward. How would it replace his presence, not to mention his role as a potential love interest for Rebecca?

Enter Scott Michael Foster as Nathaniel Plimpton.

He burst onto the scene as Rebecca’s rude boss at the law firm midway through season 2. The show’s characters voiced the audience’s trepidation in song form at having to invest in a new character who may or may not work on the show’s carefully cultivated wavelength.

Those fears were put to rest the second it became clear Foster had both the musical and comedic chops to hang with the West Covina gang. The exact moment that happened was the hilarious “Let’s Have Intercourse,” a parody of Ed Sheeran’s “Thinking Out Loud” video where Nathaniel couldn’t sound more bored about the notion of hooking up with Rebecca.

As he and Rebecca’s relationship progressed and Josh became a less viable contender for Rebecca’s heart, it seemed like Nathaniel might be her romantic endgame. They came so close to beginning a healthy relationship a few times, including when they declared their love for each other right before Rebecca pleaded guilty to attempted murder (long story).

That idea became less realistic when Greg returned in the form of Astin. Again, the show had to find a way to integrate a new face into its established cadence, this time pretty late into its run. It also had to justify why Greg was an entirely different person.

Once again, Crazy Ex-Girlfriend proved it was up to the task. Astin and Bloom had chemistry for days, which the two immediately showed in the adorable number “Hello, Nice to Meet You.” This Greg fell right back into the old Greg’s life like he had never gone off to business school in Atlanta.

Some shows would crater under the weight of having to reconfigure themselves on the fly this many times. Yet Crazy Ex-Girlfriend consistently stuck the landing, always rewarding its audience’s faith in its ability to maintain its high standards regardless of the adversity it faced behind the scenes.

It’s a small miracle that Crazy Ex-Girlfriend was allowed to be any version of itself. It had everything going against it and still continuously proved its doubters wrong at every turn.

Here’s to Crazy Ex-Girlfriend, a show that’s destined to go down as the overlooked masterpiece of the prestige TV era.