Actor Ben Stiller plays a grumpy misanthrope in his new film, Greenberg. (Axel Schmidt/AFP/Getty Images)

With his hunched shoulders and Neanderthal face, Ben Stiller perfectly embodies the schlemiel he typically plays. It’s easy to forget he’s one of Hollywood’s most bankable leading men.

Since the early 1990s, the actor has carved out an unlikely career, starring in everything from gross-out comedies (There’s Something About Mary), to kids’ films (Night at the Museum) to date movies (Along Came Polly).

His latest project is Greenberg, which opens this Friday. In the film, which was written and directed by indie auteur Noah Baumbach (The Squid and the Whale), the 44-year-old Stiller plays Roger Greenberg, a toxically bitter erstwhile musician. Anxious, self-absorbed and socially inept, Greenberg is the distillation of the omega male roles that have made Stiller famous. From the brainless but “really, really, really ridiculously good-looking” male model Derek Zoolander to the hapless, humiliated son-in-law Greg Focker, Stiller’s body of work has been a study in short-fused, long-suffering loserdom.

The Ben Stiller Show (1990-1991, 1992-1993)

This short-lived but influential sketch comedy show was the launching pad for Judd Apatow (who co-created it with Stiller), Janeane Garofalo and Andy Dick. Alongside spoofs of celebrities like Tom Cruise and William Shatner, the show featured a skit in which Stiller played the tragic “sixth Backstreet Boy”; another brilliant send-up was a mockumentary about U2, starring Stiller as a preening Bono.

Reality Bites (1994)

This mopey ode to Gen X navel-gazing was Stiller’s directorial debut. He portrays Michael Grates, a wunderkind executive on an MTV-style channel, who falls for a wannabe filmmaker played by Winona Ryder. Strangely, Stiller is the nice guy who finishes last. Here, it’s Ethan Hawke’s Troy, an unemployed snob who sneers through his facial hair, who serves as the proto-Roger Greenberg.

Flirting with Disaster (1996)

Stiller had his first leading role in this antic screwball comedy written and directed by David O. Russell. He plays Mel Coplin, a confused new father on a quest to find his birth parents, aided by an incompetent social worker (Tea Leoni) and a pair of gay federal agents (Richard Jenkins and Josh Brolin). The biological parents turn out to be played by Alan Alda and Lily Tomlin, who reveal that Mel was placed for adoption after their arrest for manufacturing “a very small amount, relatively,” of LSD.

The Cable Guy (1996)

Stiller has a small role in this film he directed about a screw-loose cable installer (Jim Carrey) who develops a creepy man-crush on a client (Matthew Broderick). A few shades too dark to succeed as a mainstream comedy — The New York Times said “it offers the shocking sight of a volatile comic talent in free fall” — the film reveals the dark side of Stiller’s comic sensibility.

Permanent Midnight (1998)

In a rare dramatic role, Stiller plays Jerry Stahl, the real-life TV writer and heroin addict. Stiller brings a feral quality to his portrayal of Stahl — a man so in thrall to his demons that he tows his kid along in the car when he goes out to score drugs.

There’s Something About Mary (1998)

That this film came out the same year as Permanent Midnight is proof of Stiller’s range. In this Farrelly Brothers comedy, Stiller is the ur-nerd Ted, whose pre-date preparations turned “hair gel” into a dirty joke.

Meet the Parents (2000) and Meet the Fockers (2004)

Greg Focker is the quintessential Stiller Everyschmuck, knee-deep in a septic tank overflow of his own making.

Zoolander (2000)

Playing a himbo on a mission, Stiller also directed this gently demented parody of the fashion industry. Best line? After delivering an address at a funeral, Derek Zoolander refers to himself as a “eugoogleizer.” Best scene? See above.

The Royal Tenenbaums (2001)

Wes Anderson’s obsessively created jewel-box universes of angst can be overly precious. This film, however, has just enough sputtering rage — in the form of Stiller’s Chas Tenenbaum, one of a trio of siblings traumatized by their dysfunctional dad (Gene Hackman) — to keep it more cutting than cute.

Along Came Polly (2004)

Stiller has yet to be entirely convincing as a romantic comedy lead. Exhibit A: This stinker, in which he plays an uptight germaphobe to Jennifer Aniston ferret-loving free spirit. (Also see: If Lucy Fell, Keeping the Faith and The Heartbreak Kid.) Maybe it’s his knee-jerk mockery of his own considerable charms. Maybe it’s his chronic chemistry problems with his leading ladies. Or maybe it’s that Stiller’s go-to toilet humour has no business in a date movie.

Curb Your Enthusiasm (2004–2007)

Stiller plays “Ben Stiller” in a recurring role on Larry David’s cringe-comedy series. Turns out that “Ben Stiller” is a petty, controlling sulk. Is this a case of art imitating life?

Night at the Museum (2006) and Night at the Museum: Battle of the Smithsonian (2009)

Even in a kids’ movie, Stiller can’t go saccharine. This blockbuster franchise about exhibits that come alive in the night kicked off with a slightly sour premise: Stiller plays a resentful divorced dad forced to take a job as a museum security guard to meet his child support payments.

Tropic Thunder (2008)

Stiller directs and stars as a smug, washed-up action movie hero in this war movie satire that features “retard” jokes, Robert Downey Jr. in black face and an unrecognizable Tom Cruise as a bilious studio executive. Most offensive of all, though, is this bloated Hollywood product trying to pass itself off as a parody of celebrity excess.

Rachel Giese is a writer based in Toronto.