Will Ben Stiller Ever Be Funny Again?

Ben Stiller sucks. But he didn't used to.

I used to lump Ben Stiller in with all the other prominent cases of comic arrested development: Adam Sandler, Jack Black, and Will Ferrell. Four "actors" whose acting repertoire at this point in their careers consists of only one character, the same character: an emotionally stunted man-child whose petulant rage, repression, and cluelessness is played for laughs. All four come out of a sketch comedy background, so if you dig out the DVDs you can see that they all had much greater versatility at one point in their lives. Now they're all stuck in permanent repeat.

But Ben started out with (and squandered) more talent than the rest of them combined. As a writer, director, and sketch comedian, he was one of the brighter lights in an early-'90s artistic renaissance that gave him plenty of competition, the brief moment of Generation X's cultural ascendancy prior to being relegated to VH1 "I Love The" specials. His downward spiral hasn't been as precipitous and jaw-dropping as Mike Meyers' horrifying freefall; it's just been steady, and infuriating.

After a cup of coffee with Saturday Night Live in the late '80s, he starred in, cowrote and produced one of the great lost sketch comedy shows, the legendary Ben Stiller Show, on the air for just one season in 1992. On its cast and writing staff were Stiller, Janeane Garofalo, Andy Dick, Bob Odenkirk, David Cross, and a 24-year old Judd Apatow. Stiller's then-girlfriend Jeanne Tripplehorn frequently cameoed on the show. Dick and Garofalo have become two more casualties of the Gen-X early peak syndrome, but back then they were absolutely hilarious. Stiller was front and center in most sketches, his face often caked in mounds of prosthetics and makeup as he did cult classic impressions of Oliver Stone, Bruce Springsteen, and Tom Cruise. The show's interstitials mostly featured Ben and the cast making fun of their likelihood of getting canceled, which of course they did. The best sketches, like "Oliver Stone Land" and "The Grungies," stand the test of time, and are well worth Youtubing.

Released two years later, Stiller's directorial debut, Reality Bites, is a bit dated in places -- particularly its idolization of then-queen Winona Ryder -- but it somehow holds up nonetheless. It has a terrific cast, including Garofalo, in her screen debut, and is a quintessential movie of its times. (There's even a cameo by Evan Dando.) The movie's also genuinely sweet. In a winning bit of humility, Stiller casts himself as the requisite unfunny sellout, a young guy who's a corporate executive, who looks for and provides nothing more than boring emotional stability. But his mature willingness to cede the spotlight seems to have disappeared as he's become a bigger star.

Around the middle of the decade it started to go south. In 1996, Stiller directed one of the decade's bigger bombs, the Jim Carrey disaster The Cable Guy, but rebounded two years later by starring in one of the most successful comedies of all time, the Farrelly Brothers' There's Something About Mary, which the American Film Institute named the 27th best comedy of all time. By that point, he wasn't just a star among disaffected twentysomethings -- he was becoming an above-the-marquee name, and the quality of his filmography began to dip. In the same year, he released a prestige piece, the heroin drama Permanent Midnight, which bombed utterly. So did the following year's critically panned superhero comedy Mystery Men, but Stiller's role in that movie was telling: he played a superhero named "Mr. Furious," whose super power was getting really, really angry, a trait that nearly all of his most recent starring roles have shared.

One of the more successful of these subsequent angry, repressed, one-note leading men was Chas Tenenbaum in Wes Anderson's The Royal Tenenbaums. He took a break from angry to do clueless in the modestly funny Zoolander, and reprised his sweet, understanding turn in Reality Bites to do Edward Norton's little-seen Keeping the Faith. Otherwise, he's been cashing checks to play more or less the same character since the turn of the century in a new stinker every year: Envy, Along Came Polly (less angry, more repressed), The Heartbreak Kid, Duplex, Meet the Parents/Meet the Fockers, Dodgeball, and, for good measure, he's been in bad children's movies like Madagascar and A Night at the Museum. He's been prolific, but not at all discriminating, versatile, or interesting.

Now he's pushed his chips into Tropic Thunder, the Robert Downey-in-blackface comedy that Stiller is starring in and directing, which will either piggyback on Downey's Iron Man action-hero success, or bring back frightening memories of The Cable Guy. I want to believe that he can rediscover the effortless funny he was able to channel over early Judd Apatow jokes, even as he's been overtaken by more current Apatow it-boys like Steve Carell, Seth Rogen, and Jason Segel. I want to believe that it's possible to stay funny after the age of 40, despite the career paralysis of Stiller, Garofalo, Black, and Meyers, each of whom I adored at the turn of the century. I want to believe in Ben.

Can Ben bring back the magic? Am I a fool to hope?