Top Performances is a recurring feature in which we definitively handpick the very best performances from an iconic actor or actress.

    Ben Stiller may be really, really ridiculously good looking, but there’s something even more impressive hiding beneath those chiseled abs and stunning features. The actor’s versatility isn’t the kind of thing that shows up on a magazine cover, but it’s a huge reason why he’s been able to carve out a 30-year career that encompasses indie dramas (Permanent Midnight), satirical black comedies (The Cable Guy, Mystery Men), and parodies that walk the line between subversive and mainstream (Zoolander, Tropic Thunder). Stiller has even cornered the market on children’s entertainment, voicing Alex the Lion in the computer-animated Madagascar franchise and starring in an interminable series of Nights at the Museum. You don’t get this way by being one-dimensional, despite what the blank look on Derek Zoolander’s face might suggest.


    With Zoolander 2 set to hit theaters this week, we thought it’d be a good time to reflect on Stiller’s career and celebrate the roles that stand out from the rest. Stiller has embodied quite a few archetypes on screen — the schlemiel, the everyman, the antihero, the luckless lover — but all of his best roles reflect the same dedication to craft and character. Whether your favorite version of Stiller is Roger Greenberg or Gaylord Focker, it’s easy to appreciate the unique cocktail of humor and pathos that shows up in different potencies across all of his films. It’s just a shame he’s such a bad eugoogoolizer.

    –Collin Brennan
    Associate Editor


    10. Hal L.

    Happy Gilmore (1996)

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    “Check out the name tag. You’re in my world now, Grandma.” And so we’re introduced to Stiller’s Jekyll-Hydian Hal L., the nefarious orderly who turns the nursing home of Happy Gilmore’s sweet grandma into a godless sweatshop. What separates Hal from Stiller’s litany of abusive weirdos is both physical AND performative: the horseshoe ‘stasche, for one, deftly conveys unhinged masculinity, while his threatening demands resonate more as a twisted middle-management tactic than anything genuinely dangerous. Perhaps most importantly, Hal L. is probably one of the brightest examples of what made early Adam Sandler movies so great: the nonsensical, yet vividly drawn, supporting character. They serve no true purpose and are allotted more screen time than they deserve, but these characters are what ultimately gave the movies so much texture. Happy Gilmore’s chock-full of good lines, but they all fall behind every single one of Hal’s lines in terms of quotability. –Randall Colburn

    09. Jerry Stahl

    Permanent Midnight (1998)


    The forgotten 1998 addiction indie Permanent Midnight stars Stiller as a successful television writer whose devotion to heroin, crack cocaine, and just about everything else costs him his career and family. It was based on Jerry Stahl’s autobiography of the same name, so the film’s unfiltered look at addiction feels honest and heartfelt, but the film itself never quite transcends the traditional junkie’s redemption story. What does stand out, however, is Stiller’s performance as Stahl, which has been unfortunately forgotten along with the film itself. Credit that to the film’s poor box office performance, or that his star-making turn in the Farrelly brothers’ There’s Something About Mary came out that same year. Either way, it’s a shame.

    Stiller’s sweaty, confident performance bears few traces of the schlemiels, schlubs, and shits he would go on to play in mainstream cinema. As Stahl, the actor adopts a slick, peripatetic wit that carries him through scenes of inspiration and sick depravity, the most memorable of which find him suicidally leaping against the interior windows of a skyscraper with perennial heavy Peter Greene and shooting up junk alongside a toddler. His commitment to the film’s sun-baked filth is both astounding and unlike anything else in his oeuvre, be it comedic or dramatic or somewhere in between; I mean, where else will you see Stiller desperately flex a neck vein so he can plunge a needle into it as a baby cries next to him? Permanent Midnight isn’t perfect, but it does offer a glimpse at the risky, Oscar-chasing dramatic actor Stiller could very well have become had the film taken off. –Randall Colburn

    08. Gaylord “Greg” Focker

    Meet the Parents (2000)


    The most hapless iteration in a long line of Stiller everymen, Gaylord Focker spends most of Meet the Parents in a war of attrition with his girlfriend’s father, Jack (a gleefully hammy Robert De Niro). Jay Roach’s film exaggerates the anxieties that come with meeting the parents, but it also takes pains to create characters that are realistic and sympathetic. Stiller’s Focker suffers a laundry list of indignities during his weeklong foray into boyfriend hell, from jokes about his profession as a male nurse to a polygraph test in which he’s asked if he’s ever watched pornography. But something interesting happens along the way: Focker slowly transitions from fool to hero, persisting until he finds his place in a family that does everything it can to exclude him.

    Despite all the outlandishly embarrassing situations he finds himself in, Stiller seems more comfortably himself in Meet the Parents than in any of his other major roles. One of the film’s many strokes of genius is to use Stiller’s own Jewishness as the springboard for a culture clash, with implications that extend far beyond their comic effect. More relatable than the typical Woody Allen protagonist but just as neurotic, Focker is the ultimate example of Stiller’s ability to generate humor and pathos all at once. –Collin Brennan

    07. Mel Coplin

    Flirting with Disaster (1996)

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    In this underseen and oft-forgotten satire from director David O. Russell (now riding high with his Jennifer Lawrence trilogy of Silver Linings Playbook, American Hustle, and Joy, so don’t feel too bad for him), Stiller is the maladjusted protagonist, Mel, whose natural edginess makes a good proxy for Russell’s. Mel is the adopted son of overanxious Jewish New Yorkers (Mary Tyler Moore and George Segal), who despite his life of privilege feels that he cannot have sex with his wife (Patricia Arquette) nor name their infant son until they embark on a cross-country road trip to find his biological parents. Along the way, Mel and Nancy navigate attractions to others — Mel to the sexy adoption counselor (Téa Leoni) and Nancy to her bisexual friend from high school (Josh Brolin) — and cases of mistaken identity with several would-be parents ensue.

    Mel should be more annoying than he comes across, but Stiller anchors him in the endearing style for which he has become known: neurotic, inescapably Jewish, and so easily befuddled that one hopes he will succeed just so he will feel a bit better about himself. Any actor who earns empathy while playing a lying, cheating asshole has talent; that Stiller has played versions of this character multiple times and is still so beloved makes him a master of his craft. –Leah Pickett

    06. Josh Srebnick

    While We’re Young (2014)


    In what Noah Baumbach calls his “most accessible film,” Ben Stiller happens to play his most accessible character. Josh Srebnick is a floundering middle-aged filmmaker who’s seduced into thinking that he can live his 20s all over again (Spoiler Alert: He can’t). A more subtle and nuanced take on Stiller’s typical role of schlemiel, Josh doesn’t realize that the joke’s on him until it’s too late. Neither does the audience, for that matter, thanks to the wide-eyed complexity Stiller brings to his role. For a long moment in the film’s first half, we find ourselves poring over the same questions as Josh, wondering what’s so wrong with living life to the fullest and owning a huge collection of vinyl records to boot. Anyone who’s ever feared the prospect of getting old and losing touch — and let’s admit it, that’s pretty much everyone — can find something to relate to in Josh, making him the most successful example of Stiller’s recurring everyman. –Collin Brennan

    05. Tony Perkis

    Heavy Weights (1995)

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    Where to begin with Stiller’s most underrated performance, as a psychotic fat camp director in the 1995 cult classic Heavy Weights? Channeling a wigged-out Tom Cruise a decade before his first Scientology video, Stiller makes entrepreneurial fitness guru Tony Perkis a hysterical villain for the ages.

    “Being an only child, educated entirely by private tutors my whole life, I’m looking forward to interacting with children for the first time,” Tony announces, infomercial-style, during his introductory assembly. Unsurprisingly, his leadership quickly turns tyrannical, as he severs his campers from the outside world, raids their cabins to remove calorific treats, forces them to complete brutal exercise routines that border on sadistic, and even goes as far as to imprison naughty boys in a makeshift cell, à la Miss Trunchbull in the similarly dark Matilda (1996).

    The Disney-produced farce, co-written by Judd Apatow, has the noble distinction of being loathed by critics and, despite a dismal box office showing, adored by audiences, holding a 29 percent critics rating and a 79 percent community rating on Rotten Tomatoes. Perhaps the subject matter alarmed first-run theatrical goers who went in expecting another generic, family-friendly romp typical of Disney at the time. But had it not been for Stiller’s insane performance transmuting the film into a zany black comedy that both quirky kids and adults could enjoy, cult status likely would have eluded this deserving gem and made it just another $2 DVD buried in the bargain bin. Fortunately, Stiller and Apatow diehards know better.


    P.S. Fans of Dodgeball: A True Underdog Story (2004) should also note that Stiller’s White Goodman is essentially Perkis 2.0 with a handlebar mustache. –Leah Pickett

    04. Chas Tenenbaum

    The Royal Tenenbaums (2001)


    Something Stiller’s always understood is how integral appearance is to a memorable comedy character. His overtly comedic characters almost always bear some kind of physical hallmark, whether it’s Tony Perkis’ audacious ‘do or the aforementioned horseshoe ‘stasches of Hal L. and White Goodman. Similarly, what most people associate with Stiller’s turn in Wes Anderson’s 2001 dramedy The Royal Tenenbaums is the bright, red Adidas tracksuit worn by his Chas and the character’s boys. But, as is the case with most of Anderson’s work, what begins as a charming sight gag eventually transforms into something much more resonant: Chas, scarred by the shocking death of the boys’ mother, is desperately trying to mold them in his own image, if only to ensure they never stray too far.

    Chas is all blunt edges, and Stiller’s overprotectiveness and hysterical “safety drills” alternate between hilarious and terrifying as the film progresses. But all it takes is a single line for Stiller to articulate his character’s borderline-abusive tendencies: “I’ve had a rough year, Dad.” It’s his first adult moment of genuine connection with Gene Hackman’s Royal Tenenbaum and a moment so vulnerable that it feels as if he’s risking his life just by saying it. All of Chas’ pain, fear, and desperation flickers and fades in the course of those six words, and it marks the most moving moment in a film full of them. –Randall Colburn

    03. Derek Zoolander

    Zoolander (2001)


    Aside from being really, really ridiculously good looking, Derek Zoolander is probably Stiller’s most iconic role. The sheer number of Zoolander quotes that have seeped their way into popular consciousness is staggering, and most of them belong to the titular character himself. But why has this harmless send-up of the fashion industry become such a zeitgeisty hit, and why has Stiller’s dimwitted male model endured as one of the most beloved comic characters of the 21st century?

    The answer probably lies in the absurdity of the premise. Stiller is by no means bad looking, but the fact that a short Jewish man can play the most popular model in the world is the unaddressed joke at the core of the film. Here’s the amazing part: Stiller embodies the role so fully that we actually start to believe it. It’s fun to watch an actor who’s typically known for his relatability flip the script and transform into an exaggerated counterpoint of the everyman. It doesn’t hurt to mention that Stiller also directed Zoolander, carrying the film to the finish line from both sides of the camera. –Collin Brennan

    02. Ted

    There’s Something About Mary (1998)


    In the 1998 sleeper hit that shot both Stiller and co-star Cameron Diaz to the top of the comedy A-list, Stiller proved that his years of hard work in television (The Ben Stiller Show), film directing (Reality Bites and The Cable Guy), and acting in mostly underappreciated black comedies (Flirting with Disaster, Your Friends & Neighbors, etc.) were not in vain. As the hopelessly romantic and perpetually hapless Ted, Stiller also cemented his place in the pop culture lexicon. Bathroom-before-prom scene, masturbation-before-date scene, picking-up-a-hitchhiker-gone-awry scene — take your pick.

    Though helped in large part by the Farrelly brothers’ brilliantly perverse writing and directing, the majority of the gross-out gags and over-the-top slapstick would not have worked without Stiller’s razor-sharp comedic timing and uncanny ability to stick his landings. His physical comedy in particular is astounding; if one is so inclined, re-watch the extended dogfight and “hair gel” clips on YouTube to affirm. –Leah Pickett

    01. Roger Greenberg

    Greenberg (2010)


    Roger Greenberg isn’t just Stiller’s best character; he’s one of the greatest characters to grace a 21st century cineplex. Emotionally scarred, unrelentingly bitter, and endlessly contradictory, Greenberg is the kind of monster who’s spent the bulk of his adult years callousing himself against the world based on the dumb decisions of his youth, the ideals of which still choke him to such a point that he can barely breathe among millennial society. To admit you empathize with such a dickbag is to reveal something unsavory about yourself, so both the character and movie were unfairly derided by casual audiences. Or maybe just young ones. Despite the presence of wunderkind Greta Gerwig, Greenberg isn’t for kids.

    In the grand scheme, Stiller’s prickly, breakneck performance as Greenberg is redolent of his work on The Royal Tenenbaums and another Noah Baumbach joint, While We’re Young. In all of these movies, Stiller expresses fears of aging and instability by pinning a psychological undercurrent to the native neuroticism of his lighter fare, thus transforming affable awkwardness into paranoia and psychosis. Navigating this so well is Stiller’s greatest gift as a dramatic actor and what allows him to be one of the rare performers whose career can toe the line between big-budget schlock and art-house nuance.

    “I think you’re mean,” Greenberg says during the film’s most memorable scene, which finds the 40-year-old partying with a bunch of teenagers. He’s speaking to all of them, shaming them not for making fun of his taste in music or fashion sense, but for proving to him just how irrelevant he’s become in life. He’s speaking to youth in general and, as he does in The Royal Tenenbaums, imparts a life’s worth of philosophy in just a few words. Acting isn’t crying and shouting. Acting isn’t saying meaningful words. Acting is unpacking humanity. Sure, Stiller might not be doing that in Night at the Museum, but he’s most surely doing it here. –Randall Colburn