“I have trouble living in the present, so I linger on the past,” says Roger Greenberg (Ben Stiller) in 2010’s Greenberg. Roger, whose irascible solipsism prevents him from actual growth, isn’t the only one. Across five romantic comedies in the mid-’90s, Stiller refined his star persona as a romantic lead, carefully sanding down the rough edges. Beginning with Reality Bites and continuing through Meet The Parents, Stiller played variations of insecure neurotics thrust into uncomfortable situations they either caused or intensified. As his romantic lead career went on, Stiller found ways to glean sympathy from humiliation in his screwball love triangles—or, in the case of There’s Something About Mary, love pentagrams.
Stiller didn’t arrive in Reality Bites fully formed. The son of comedy greats, Stiller was a child and teen performer before landing a brief stint on Saturday Night Live. The next year, he brought his sketch series, The Ben Stiller Show, to MTV. Stiller then put his sketch comedy expertise to work in Reality Bites, directing himself as Michael, an ineffectual, put-upon TV executive, and the other man in a love triangle with will-they/won’t-they college couple Lelaina (Winona Rider) and Troy (Ethan Hawke).
Stiller blends into the ensemble, never pulling focus from Lelaina as he serves her story. But he’s also, at first, the likable alternative to Troy. Michael isn’t a stereotypical coke-snorting executive, but soft-spoken and afraid to offend. As in their car crash meet-cute, he’s spinning too many plates, constantly besieged by the world around him despite his attempts to please whoever is in front of him. However, his relationship with Lelaina is transactional. Michael, who gives her documentary to an MTV analog without her permission, thinks tit-for-tat is how romance works. When the network ruins her vision, Stiller puts on an air of self-righteousness: “I feel like maybe I deserve another shot here.” Michael is an option, but he represents something no self-respecting Gen X-er could ever love: a sellout.
In Michael, Stiller demonstrates the sensitivity and sanctimoniousness he’d weaponize to even more unlikable ends in Flirting With Disaster. Upgraded from supporting player to full romantic lead, Stiller plays adopted entomologist Mel Coplin, the father of a newborn he can’t bring himself to name and adulterous husband of Nancy (Patricia Arquette).
A screwball romance in the Bringing Up Baby mold, Flirting With Disaster sees Mel balance his decaying lust for his wife with his sudden attraction to Tina (Téa Leoni), an inept but sexually virile adoption agency rep promising to reunite Mel with his birth parents. His behavior is so gross that the chance that Nancy might leave him for an armpit-obsessed high school sweetheart (Josh Brolin) seems like a viable option.
Though Stiller plays a bigger cad here than in Reality Bites, he is the film’s star and therefore entitled to its happy ending. Mel, with his sense of boyish enchantment whenever he meets another new person who might be one of his parents, makes the comedy of remarriage work thanks to his chemistry with his costars. There’s heat between Stiller and Leoni, but the warmth with Arquette leads the film towards its eventual reconnection.
More of a sex farce than a screwball, There’s Something About Mary adds more suitors for Stiller to worry about and makes him the best option by comparison—a step up from Flirting. He plays Ted, a self-described stalker who missed his shot with Mary (Cameron Diaz) after his zipper and junk had a meet-cute. The missed connection haunts Ted into his 30s, so Ted hires a private detective (Matt Dillon) to track her down. The “something” about Mary is that all the lovestruck men in her life are deceiving her, making Ted better by default. He’s less threatening—sort of—than the pizza delivery boy (Lee Evans) posing as a disabled British architect, or the high school boyfriend (Chris Elliot) against whom she has a restraining order. In an inverse of Reality Bites, Stiller’s character learns that love is not about what he can offer Mary, but what she actually wants.
Over the course of this lesson, Mary physically punishes Ted at every turn. The hostile universe that plagued Stiller in Reality Bites and Flirting With Disaster grows even more pitiless as the ’90s wear on. Prom night turns into WrestleMania, while a misunderstanding with the police sees Ted’s head repeatedly slammed against a steel table. Framing him in wide shots so the audience can better see Stiller’s body pummeled and disgraced, the Farrelly brothers make it hard not to feel some sympathy for the guy. Even his penis is out to get him, hiding cum behind his ear like a perverted magic trick. Ted’s trials are so relentlessly punishing and humiliating that the movie seemingly lets him off the hook for stalking Mary. He’s an underdog forced to climb out of his own misogyny—a complete face turn for Stiller that he’d carry into his next rom-com.
Edward Norton entirely strips Stiller of thorniness in his treacly directorial debut Keeping The Faith. Rabbi Jake pushes Stiller entirely into hero territory as he navigates a love triangle with his priest best friend (Norton). He’s neither scheming like Ted or Mel nor unconsciously selfish like Michael. Instead, Jake worries about real problems that a young single rabbi might face, primarily how his congregation would feel about his interfaith relationship with Anna (Jenna Elfman). Free of Farrelly farce, Keeping The Faith allows Stiller to be confident, ambitious, and sympathetic. It’s a sensitive performance grounded in reality, pulling him farther away from the morally dubious men of his comic past.
Released six months after Keeping The Faith, Meet The Parents blended Jake’s sweetness with a more conventional Ben Stiller-style neurotic. Meet The Parents is firmly on Stiller’s side, introducing him as a diligent, gentle nurse and a conscientious-to-a-fault partner to Pam (Teri Polo). There’s no love triangle at the onset; he has the girl and is ready to settle down. But by asking his father-in-law’s (Robert De Niro) permission to propose to Pam, he creates a triangle between father, daughter, and future son-in-law, in which Greg must prove himself man enough to win the girl he already has.
Greg isn’t a bad guy, but Pam’s family engages him in bad faith, treating everything from his Judaism to his given name as an affront. By this point in his rom-com career, Stiller has gone from asshole co-conspirator to straight-up victim; the film is less concerned with relationships than with low-brow comedy based around emasculating Greg, which Stiller plays up through an increasingly frantic and outlandish performance. But unlike the similarly punishing Mary, Meet The Parents made Ben Stiller a family-friendly comedy star, allowing him to refine his softer persona further in family movies like Night At The Museum and the two Fockers sequels. By turning him into the humiliated victim of PG-13 comedy instead of a secret rom-com villain in search of modest redemption, Stiller could now be seen as a put-upon everyman the whole family could enjoy.
Eventually, Stiller would push back on this evolution. Greenberg—like those earlier roles of Michael, Mel, and Ted—believes he’s been screwed out of the life he deserves, pursuing a younger woman (Greta Gerwig) who suffers the same post-grad listlessness as Lelaina did in Stiller’s directorial debut. In Greenberg, he strips away all the charm and exclusively delivers distilled, sarcastic neuroticism. He’s rude, narcissistic, and constantly at odds with the life he believes he deserves, continually criticizing the decisions of others as the world passes him by. Greenberg released a few months before Little Fockers, putting Stiller’s polarized archetypes—his edgy early days and his late-career softness—on the big screen during the same year.
Throughout the 2000s, Stiller’s career bifurcated into a branch of character comedies about egomaniacs (Zoolander, Tropic Thunder) that offered a refuge for the darker sides of his comedy. What remains are his romantic leads, who absorb and exploit the emotional terror of falling in love. Stiller thrives at these neurotic extremes, earning our sympathy even when his characters don’t deserve it. Whether he’s the victim or the villain, heartbreaker or brokenhearted, in the romances of Ben Stiller, love is pain.
