The Best and Worst of Ben Stiller, A to Z

From Alex the Lion to Zipper, an alphabetical breakdown of 'Zoolander 2' star's career

Credit: DreamWorks/Photofest, 20th Century Fox/Photofest, Mary Evans/Paramount Pictures/Ronald Grant/Everett

Ben Stiller's professional onscreen career is officially turning 30 this year — that's roughly 412 in comedian years. In a business where funny people tend to quickly exhaust their limited charm and sink from telling jokes to becoming a punchline, the restless and versatile Stiller has managed to sustain one of the most consistent comic careers this side of Bob Hope. From his days as a bit player to his later emergence as a force of nature in front of the camera and behind the scenes (you have his production company Red Hour to thank for recent Comedy Central highlights Another Period and Big Time in Hollywood, FL), the man who invented Derek Zoolander — all due respect, Mugatu — has made himself into one of contemporary pop culture's most indispensable figures.

With Zoolander 2 now in theaters, we've taken a step back to bring you the ultimate overview of his working life — from Madagascar's Alex the Lion to that zipper scene from There's Something About Mary, it's an alphabetical breakdown of best (and worst) of Stiller's creative life and career.

A for Alex the Lion
Stiller might not be remembered for his voice work as a singing zoo lion in Dreamworks' animated Madagascar trilogy, though anyone under the age of eight is a big fan (as is his accountant — the movies grossed almost $2 billion at the box office, i.e. one billion for each kid whose college education Stiller will eventually have to pay for). The actor did everything he could to make these movies better, even roping in his Greenberg collaborator Noah Baumbach to punch up the script for the third installment.

B for The Ben Stiller Show
A hilarious alt-comedy hodgepodge that introduced the world to Andy Dick and Janeane Garofolo (in addition to first introducing Bob Odenkirk to David Cross), Stiller's sketch show died twice before it could live forever. First launched on MTV in 1990 before its brief resurrection on Fox a few years later, it was an unsupervised mess of pop-culture parodies, music videos, and endless Star Trek gags. Paving the way for everything from Mr. Show to Adult Swim, this cult-TV curiosity announced Stiller as a generous comic talent who's most comfortable when he's given total control.

C for "Como estas, bitches!"
Anchorman is peak Will Ferrell from the moment it starts, but the movie doesn't truly achieve greatness until Ron Burgundy finds himself in the middle of a royal rumble with all of San Diego's TV news teams. That's when mustached Spanish language anchor Arturo Mendez arrives on the scene looking like the bastard offspring of Tony Montana and Indiana Jones. Stiller only needs a single line to immortalize the character on ill-advised t-shirts you might have worn in college.

D for Derek Zoolander
"I'm pretty sure there's a lot more to life than being really, really, ridiculously good looking, and I plan on finding out what that is." With those inspirational words, cinema's most beloved male model set out on a quest that would change the world forever. Physically flawless and technically sentient, Stiller's high-concept moron may not have been an instant favorite (releasing the film in the immediate wake of 9/11 didn't help), but Derek Zoolander has since become an icon of contemporary comedy and fashion-conscious narcissism. Just say the words "Blue Steel" to anybody and watch what happens.

E for "Eating Success for Breakfast"
Imagine Dodgeball, but with overweight kids instead of scrawny adults — that's 1995's Heavyweights, which allowed Stiller to practice the psychotic fitness guru archetype that he'd later perfect with White Goodman. As Tony Perkis, a chubby kid who grew up to be the militant fitness instructor of the country's worst fat camp, Stiller gets to spout all sorts of ridiculousness at his tween charges ("Attention campers, lunch has been cancelled due to lack of hustle. Deal with it.") But the character's defining moment comes as he slaps on a mic and speaks to the kids like a coked up Tony Robbins, indelibly regaling the crowd with his personal story of triumph: "Kids, at age 12 I weighed 319 pounds. I had bad skin, low-self-esteem, and no self-respect. Now, I eat success for breakfast! With skim milk."

F for "Full Retard"
A passion project for Stiller (he also produced, co-wrote, and starred in the 2008 hit), Tropic Thunder is full of a number of inspired comic turns, from Stiller on down to whoever played that vulgar Les Grossman guy (more on him later) — but the film's legacy unquestionably belongs to Robert Downey, Jr. Playing Kirk Lazarus, an intense method actor who's taken blackface to a new level in the film-within-a-film war epic, Downey offers Stiller's character career advice about choosing Oscarbait roles that has since become a catchphrase: "Never go full retard." Say what you will about his choice of words, but the man has a good point. Just ask I Am Sam's Sean Penn.

G for Greenberg
No character has let Stiller mix his flair for raw pathos with his instinct for comedy like the misanthropic title role he played in Noah Baumbach's acidic seriocomedy. Bitter, on the mend from a nervous breakdown, and totally hot for his brother's handywoman (Greta Gerwig), Roger Greenberg provided Stiller with the perfect vehicle to go full curmudgeon. If you squint hard enough, you can almost see the man he might have been had the whole "become a rich and famous comedy icon" thing not worked out.

H for Heat Vision and Jack
The one and only episode of this failed 1999 TV show has managed to earn more rabidly obsessive fans than some long-lasting network sitcoms. Written by Community godhead Dan Harmon and directed by Stiller, the delirious pilot stars Jack Black as a super-intelligent astronaut whose slacker roommate is transformed into a talking motorcycle (and subsequently dubbed "Heat Vision," natch). Clearly, this gem was too good for our godforsaken world, but you can still watch all 30 minutes of its glory on YouTube.

I for Zoolander Instagram
Stiller's social media game is solid enough — he may not work it like Anna Kendrick, but there are definitely signs of life behind those tweets. His male model alter-ego, on the other hand, is pretty much the reason why Instagram was invented. Chronicling the production and release of Zoolander 2, Derek Zoolander's account flips between narcissism, self-promotion, and random shots of hippos more fluidly than any real celebrity could ever dream. We may never know the name of the Paramount publicity intern who's running this thing, but they've got a brilliant feel for fame. (Bonus points for the mosaic of photos in which Zoolander wears a wolf fur coat while holding an adorable baby wolf.)

J for Jerry Stahl
The Cable Guy proved that Stiller could go dark, but audiences still weren't ready for his turn as Jerry Stahl, the real-life TV writer whose memoir about addiction in Hollywood was the basis for 1998's Permanent Midnight. The live-wire drama gave the actor a dramatic part in which he could dive headfirst into the intensity that percolates beneath his funniest characters. He's never gone this dark again —it's one thing to play an acerbic character with problems, and it's another to play a guy who shoots up (into his neck!) in the front seat of his car as his baby daughter cries beside him. But good casting is good casting, and Stiller sells every bleak-as-fuck moment.

K for Kate & Allie
Although Stiller's name didn't mean all that much until he put it in the title of his variety show, he had already amassed a solid list of credits before MTV handed him the keys to the kingdom. Early appearances include bit parts in Steven Spielberg's Empire of the Sun, and the Patrick Swayze vehicle Next of Kin. He even played a character named Fast Eddie Felcher on an episode of Miami Vice before landing his writing gig on SNL. But for Stiller's very first on screen appearance, you have to go back to this long-running but largely forgotten Eighties sitcom, in which Stiller appeared in a 1986 episode called "Too Late the Rebel." 

L for Longest Selfie Stick
Stiller's legacy seemed in danger of slipping a little during his The Watch/Walter Mitty years, but the London premiere of Zoolander 2 ensured that future generations will tremble at his accomplishments. Surrounded by movie stars and fashion icons, Stiller stood in the middle of Leicester Square, held a 28-foot metal pole in his hand, and snapped the Guinness World Record for the Longest Selfie Stick ever used. A dumb stunt? Sure. But there's no denying that Derek Zoolander would be proud.

M for "Milkshake"
"Want a little somethin' somethin' for the ride home?" Years before Marvel made closing credit stingers a multiplex fixture, Stiller delivered one of the most memorable — and most disgusting — of them all in Dodgeball: An Underdog Story. Following a Hollywood ending that sees his meathead Globo Gym honcho White Goodman lose the big tournament to the Average Joes, the villain makes a not-so-triumphant return to the screen. Buried inside a mammoth (and hauntingly greasy) fat suit, surrounded by potato chip wrappers, and wearing nothing but an open robe, Stiller gives White the last word. Kelis' career has yet to recover from what happens next.

N for New York City
You can take the kid out of New York, but you can't take New York out of the kid. That didn't stop a young Ben Stiller from trying — he ditched the East Coast as soon as he graduated high school — but he didn't even make it through his freshman year at UCLA before deciding that he belonged back home. A diehard New York sports fan (his Knicks fandom is on par with Spike Lee's, and he's cited the Yankees' late-Seventies World Series runs as the happiest moments of his life), Stiller continues to work in the city whenever possible. No wonder he nailed the role of Roger Greenberg, one of the movies' most painfully uncomfortable LA transplants. We thank the Big Apple for giving our man Ben the endless fodder for neurotic comic inspiration.

O for "The One with the Screamer"
Unwittingly practicing for his future alpha douchebag villains, Stiller popped up in a 1997 episode of Friends as Tommy, a seemingly nice guy whose gentle demeanor hides a raging temper. His moment of glory comes when the gang walks in on him screaming at Joey's adorable pet chick. Not only did the setup allow Stiller to show off the comic intensity that would come to define his work, but — compared to the rest of Rachel's disposable love interests — Tommy was also still something of a catch.

P for Parents
His mom (the late Anne Meara) and dad (the seemingly immortal Jerry Stiller) were a legendary comedy team in the Fifties and hardworking performers long after that, and they gave their son every chance to build on their success. They even pop up in his movies, and sometimes even clinch their greatness — Jerry Stiller's performance as Zoolander's Maury Ballstein is a masterpiece unto itself. The way he delivers lines like "I've got a prostate the size of a honeydew and a head full of bad memories" should be studied in schools.

Of course, those aren't the only parents to whom Stiller will forever be in debt. As much as he (and we) might want to forget about the Focking sequels that followed, 2000's Meet the Parents was the kind of monster hit that enshrined its star's place on the A-list. Part rom-com and part humiliation porn, it helped Stiller find the sweet spot between comic relief and leading man.
 
Q for Quickies
As in the memorable flyby appearances ever since he popped up for a single scene in his first movie, the aformentioned Empire of the Sun. In fact, few actors can do more with less running time: Other vintage cameos include his sadistic orderly in Happy Gilmore ("You can trouble me for a warm glass of shut-the-hell-up!"), his blink-and-you’ll-miss-it performance as a fireman in 2002’s brilliant Orange Country, the Guitar Center Sales Guy in Tenacious D in the Pick of Destiny, and popping up as himself during Steve Coogan's Hollywood success dream in The Trip.

R for The Royal Tenenbaums
Possibly the most neurotic character that Wes Anderson has ever written (and that's not a claim that we make lightly), Chas Tenenbaum allowed Stiller to explore the strained anxiety that he would channel — and significantly broaden — for the hyper-earnest klutzes he later played in rom-coms. A brilliant but  paranoid widower who's best remembered for the red track suits that he forces his kids to wear like a uniform, the part smothered Stiller's comedic energy beneath a dry varnish of depression. Ironically, it paved the way for the brightest stretch of the actor's career.

S for Smithsonian
In a time when Frozen has become the world's most relied upon babysitter, it's hard to fault a film franchise that argues the benefits of education and brings history to life for a generation of dumbstruck kids. And yet … While the Night at the Museum movies are hardly the worst studio gigs that Stiller has ever taken — of his three trilogies to date, the 2009 entry Battle of the Smithsonian might even be the best — the adventures of nighttime security guard Larry Daley are each told with a deep-seeded artlessness that cheapens the enchanted exhibits he's forced to contain. Yes, these cash cows have helped bankroll his more daring stuff, and it may have helped sour a few kids' interest in checking out the venerable museum.That doesn't make them any less painful to watch if you're over the age of 12.

T for Tom Cruise
Fact: Ben Stiller is legitimately obsessed with Tom Cruise. His fixation began back in the Eighties with a recurring series of Top Gun gags on The Ben Stiller Show. (And don't even get us started about the Few Good Scouts skit.) Then, for the 2000 MTV Movie Awards, Stiller ended his own honeymoon two days early just so he could fly to L.A. and pretend to be the notoriously gung-ho action star's inseparable stunt double. To say that the duo had chemistry would be an understatement — the comedy bit they made together has singlehandedly justified the existence of this awards show for the last 16 years. After that, it was only a matter of time before they collaborated on a movie for real, and Cruise's performance as bombastic studio exec Les Grossman in Tropic Thunder unleashes the kind of comic brilliance that makes people want to overlook so many other things about Tom Cruise.

U for Underdog
He'd played everything from toxic yuppies to overexcited males — but it was David O. Russell's nouveau screwball comedy Flirting With Disaster (1996) that proved Stiller could do triumph-of-the-underdog roles with the best of them. And once he truly find his groove as the hapless and hugely committed hero of There's Something About Mary two years later, this became his default mode (even moreso than aggressive idiots). We root for his lovelorn Mary character in spite of the story's proto-stalker storyline, and his endless streak of humiliations only makes him more endearing. Stiller could walk the line between pathetic and empathetic to a tee, and he quickly parlayed that into the Meet the Parents films, the underrated Along Came Polly, and a host of roles when he needed some quick cash between directing gigs (that Heartbreak Kid remake).

V for Viagra
Allegedly a Super Bowl 50 commercial that was "bumped at the last minute," Stiller's brand new spot for Female Viagra blurs the line between where he ends and Derek Zoolander begins (the clip is just one good Magnum away from being a cornerstone of the male model's reel). Hilariously parodying the strange delicateness of ads selling boner pills, Stiller wears a football jersey and rolls on top of a bed as he whispers heartbreaking medical statistics like: "Zero women suffer from erectile dysfunction, but 98 percent of women over 30 suffer from another condition called 'Not Being Turned on By Their Husband, Anymore.'" It's hands down one of the funniest things he's done in years. And if you want to learn more, make sure to look for Female Viagra's ad in Golf Digest.

W for Walter Mitty
Updating Steven Thurber's (very) short story into a globe-trotting opus, Stiller's faux-inspirational 2013 dramedy was a "what does it all mean?" movie for anyone who's ever confused a Hallmark card for high poetry. Artfully shot but absent the sincerity that redeems even his Envy-level misfires, The Secret Life of Walter Mitty was the first time that one of Stiller's directorial efforts felt like its edges had been sanded off. All the same, it was nice to see him try new things, and the project's modest profit suggests that Stiller can afford another turn at bat.

X for Generation X
Given how seamlessly Stiller transitioned from being a young actor to a comedy triple threat, it can be easy to forget the pivotal role that he played in the self-identification of Generation X. Reality Bites was the star's directorial debut, and the shaggy story about photogenic college grads trying to hack it in the working world quickly became synonymous with its Clinton-era moment. The movie did for irony what Easy Rider did for Harleys, its success minting Winona Ryder as the elfin Audrey Hepburn of The Real World era. Stiller's role, meanwhile, was far less hip, as he weaponized his inherent lack of coolness by casting himself as the film's token yuppie.

Y for Your Friends & Neighbors
It's a truth universally acknowledged that every actor who rose to fame in the Nineties had to survive a hyper-cynical Neil LaBute sex farce in order to officially "make" it. For Stiller, his trial by ire came in the form of this dark 1998 ensemble piece, in which he played a tragically goateed theater teacher who talks too much in bed and can't satisfy his wife — the role of a lifetime! Not only did he acquit himself well from the most unlikeable character of his career, but Jerry turned out to be an ideal audition for the (more lovable) part the actor would play in The Royal Tenenbaums shortly thereafter. As an added bonus, Your Friends & Neighbors led to what has to be the only LaBute reference in Sesame Street history.

Z for Zipper
Stiller was already a known quanity by the time he agreed to play Ted Stroehmann in the Farrelly brothers' legendary gross-out comedy There's Something About Mary, but audiences didn't truly fall in love with the guy until they watched him catch a testicle in his zipper on the way to the prom. Yes, everyone remembers the "hair gel" bit as the movie's gamechanging gross-out scene. But capped off by one of the great insert shots in all cinema, the infamous snag was the moment the world realized that Stiller would follow his characters anywhere — no matter how painful, literally or figuratively — for a good gag.