Grantland logo

Who Has the Upper Hand? Ben Stiller vs. Owen Wilson

Neurosis versus chill. Chas Tenenbaum versus Eli Cash. Range versus being Bill Murray’s son (maybe).

The Upper Hand is where we pit unsuspecting entertainers against one another to determine who currently has a greater grip on the hearts and minds of America. It’s a long way of saying X > Y. It may seem reductive, or even unnecessarily competitive, to put our gentle creators into a squared circle, but it’s a useful exercise in seeing who is doing things right, who is doing things wrong, who is doing things differently, and, of course, who is winning. At the end, a guest judge will hand down a verdict. Today’s combatants are Claire Lobenfeld, riding for Ben Stiller, and Eric Thurm, taking up arms for Owen Wilson. Judging will be Chris Ryan.

The Contestants: Ben Stiller and Owen Wilson

Domestic Box Office
Stiller: $2,790,227,515
Wilson: $2,545,277,264

Biggest Hit
Stiller: Meet the Fockers
Wilson: Night at the Museum

Most Critically Acclaimed Role
Stiller: Flirting With Disaster
Wilson: Midnight in Paris

Eric Thurm: Let’s get something out of the way, up front: Ben Stiller and Owen Wilson are at their best when they’re together. You can like their individual movies, but no one should be pretending that The Secret Life of Walter Mitty or Behind Enemy Lines is coming anywhere close to Zoolander, The Royal Tenenbaums, or even Starsky & Hutch (but we’ll get to that). Today’s Upper Hand is basically a re-creation of Zoolander’s 2001 VH1 Fashion Awards1 Male Model of the Year competition, pitting the established Stiller, who now plays “serious” roles in movies directed by Noah Baumbach, against the infinitely more chill Wilson.


An event that totally took place and was apparently important at the time.

And just as in Zoolander, the faux–New Age, Sting-ignorant underdog deserves the win. Anyone can say, “Oh, I love Ben Stiller in Dodgeball or whatever,” but does he really deserve front-runner status here? Does the guy really know how to play serious roles? Owen Wilson’s talents are deeper (and maybe better hidden), but that’s not going to stop me from digging them up and thus embarrassing you for entering into this Upper Hand on behalf of Ben Stiller. Bring it on.

Claire Lobenfeld: Both Wilson’s and Stiller’s résumés are rife with trash. To debate two guys who have both played love interests for Jennifer Aniston, in equally humiliating movies — Marley & Me for being emotional manipulation porn and Along Came Polly for its sharts — is almost silly. But to suggest that the Wilson belongs on some higher pedestal than Stiller is ludicrous. Four words for you: There’s. Something. About. Mary.

And Stiller’s character from that film, Ted Stroehmann, brings me to my next point: Being chill is overrated, Eric. Stiller’s ability to do neurosis is dynamic, well past what we get from Wilson, the dude who never grew out of his high school dorkiness. You need heroin-addled creative neurotic? Bam, Stiller as Jerry Stahl in Permanent Midnight. How about someone trying to impress his girlfriend’s parents while playing the straight man to Robert De Niro? Oh, here’s the Fockers trilogy. If you prefer your high-strung character to be one of the chosen people, allow me to suggest Greenberg. And in those flicks alone, we have four different kinds of appeal: gross-out humor, dark indie, family-friendly, and white people problems. I have only begun to scratch the surface, too. Now, please, I’d like to see some examples of Wilson’s range beyond “frat boy adjacent.” (Examples where Stiller isn’t also present. Yes, I know your boy was in Permanent Midnight.)

Thurm: Owen Wilson is always Owen Wilson. He might be riffing on an archetype (the chillest of archetypes), but “range” is totally overrated as something we expect actors to possess. Dude doesn’t need range — he has star quality. Did Gary Cooper have range? Did Jimmy Stewart? Hell, does Jack Nicholson have range? It’s all about being cast well and getting the most out of the character. Sometimes you get lucky, cast in a role that a lot of other neurotic Jewish guys probably could have pulled off, in a movie that ends up being really good. (Yes, that is me throwing side eye at Ben Stiller in There’s Something About Mary.) And that’s something for which no one ever gives Owen Wilson appropriate levels of credit.

Francis from The Darjeeling Limited? Yeah, he might have the spacey cadence that Owen Wilson is biologically and culturally forced into always employing, but he’s also playing up the earnestness of the persona you’re calling “frat boy adjacent.” Eli Cash from Tenenbaums is great because he’s a cocky, macho dude — or, as macho as one can be with fringes on one’s shirt — but he’s also trying to be an intellectual, and hiding some surprising depths. Also, when was the last time Ben Stiller did anything this worthy of a meme?

I can’t believe it even needs to be said, but let’s talk Ned Plimpton. The Life Aquatic With Steve Zissou is the most underrated Wes Anderson movie; it deserves more credit for how visually interesting it is, and also for the strength of the perhaps paternal relationship between Ned and Bill Murray’s Zissou. Is there a higher compliment you can pay an actor than to consider it plausible that he could be Bill Murray’s son? I don’t think so. Could Ben Stiller be Bill Murray’s son? Nah.

Are those all Wes Anderson movies? Yes. There is nothing wrong with knowing what you’re good at and having consistent collaborators. (Maybe Ben Stiller should pull back on his collaborations with Shawn Levy of Night at the Museum TRILOGY fame.) And if you want some real examples of range, let’s talk screenwriting. Wilson cowrote Bottle Rocket, Rushmore, AND The Royal Tenenbaums with Anderson. Those screenplays are strong, and as much as people like to mock Anderson for having a well-defined style, they’re about a bunch of different things. As good as any other actors in those movies are (hello, Chas Tenenbaum), Wilson was the person writing their parts. How is anyone supposed to come back from that?

Lobenfeld: I completely understand why you’re trying to draw attention away from the “range.” I would, too, if I were arguing against someone who starred in a classic eponymous sketch show early in his career, who directed one of the most important Gen X films of all time in Reality Bites, and who has his finger in that sweet, sweet Hulu pie as executive producer of Burning Love, proving he has no fear of the next generation of comedy greats. And you are totally right, Ben Stiller could not be passed off as Bill Murray’s son. He’s too busy being Jerry Stiller’s IRL progeny. (I’m not done, though. You can air your grievances in a minute.)

But while we’re on the subject of faux-fatherhood, I’d like to suggest that Stiller actually co-birthed Wilson’s career. After Bottle Rocket, what was Wilson’s next look? The Cable Guy, a little film starring Ferris Bueller and the Mask, DIRECTED BY BEN STILLER. My guy still hasn’t stopped looking out for the youth, either; he works with Jonah Ray and Kumail Nanjiani on their Comedy Central show The Meltdown. What has Wilson done for the next generation, aside from getting a bunch of young guns to star in a movie that was basically a Google ad, or playing a cowboy in a kids’ movie trilogy? (You can pooh-pooh Stiller’s involvement in the Museum trilogy all you want, as if Wilson isn’t in all three …)

Thurm: “Range” is a way we describe a bunch of smaller mountains clustering around the bigger mountain that everyone is actually on a hiking trip to climb, and that is the definitive word on that. Speaking of smaller peaks, who cares about the youth? I’m about Owen Wilson, and will continue to be about him, regardless of whether he entertains children with flashlights. That’s, at the most, a glorified cameo in the Night at the Museum movies. Let’s not pretend that Stiller isn’t the knight championing the TRILOGY. Besides, the most important thing either of them could have done for the children was to create Max Fischer.

All right, all right (all right): I’m not going to deny that Ben Stiller works a lot more than Owen Wilson does, which means he’s statistically likely to be in more things that succeed. But here’s the thing about Reality Bites, Permanent Midnight, Greenberg, and pretty much every other Stiller movie you could throw in that isn’t a goofy comedy (looking at you, Walter Mitty): They’re supremely, obscenely self-involved, and ultimately more about the exploration of one particular archetype (“being Ben Stiller”) than the films of Wilson’s career, which at least manage to ask what his cool-dude posturing means some of the time. The rest of the time, Wilson knows he’s in it for the money and isn’t trying to make ridiculous Oscar bait (Walter Mitty, just get out of here). I’m all for Owen Wilson doing him and being aware of who and what he is. Stay in your lane, homey.

Lobenfeld: Stiller just has a stronger will than Luke’s big bro, as evidenced by his willingness to spread himself across different aspects of his field. Ben Stiller is a dedicated Knicks fan who still sits courtside, despite the fact that this is the bunkest season in the history of the franchise. Do you know who has guts of steel? Blue (and orange) steel, if you will? Knicks fans. We are trenchant fighters who have a stick-to-itiveness that rivals almost any other team’s fans, and I think that gumption is reflected in his breadth of work. (And, not to go back to the dead-dog movie, but, like, calling characters who are depressive or heroin addicts “self-involved” is pretty gauche when Wilson is caking off of blatant emotional manipulation that’s as craven as any Nicholas Sparks dreck.)

But I digress! You mentioned Oscar bait and that is the only area in which I will concede to you: Midnight in Paris drops 10-ton anvils on The Secret Life of Walter Mitty. You have me there. And like a Stiller-esque Knicks fan, I am unafraid to admit when I have lost. Speaking of Knicks fans, however, let’s slide into the present: the Anna “Go New York, Go New York, Go!” Wintour–assisted, Zoolander 2–confirming Fashion Week walk-off. We have tangible, at least via YouTube, evidence as to who, at this very moment, has the upper hand. I’m going to go out on a limb and say: Hansel — not so hot right now. I mean, would we even be here if it weren’t for Stiller?
Thurm: If that was your Blue Steel, here’s my Magnum. For Zoolander 2 to not be a disaster of Mugatu-esque proportions, worse than those lookout models at the Kennedy assassination or last night in the tearoom, it has to be funny. And for all that he might be good at doing serious “aging man” roles, Ben Stiller has forgotten how to be funny. The world needs Hansel and his bewildering, near-magical ability to not look like a total idiot while riding a Razor scooter — now more than ever.

Lobenfeld: Listen, Stiller has funny “aging man” roles in his pocket, too. Anyone who has the gall to take his wife on International Ghost Investigators is at least fun. You know what’s not fun? Being in a Paul Thomas Anderson–directed film adaptation of a Thomas Pynchon novel. (OK, that’s totally fun, but not for the masses.) Owen Wilson, when he’s not bro-ing down with Vince Vaughn, appeals to the midbrow almost always. I will admit that a lot of his work is very good — Inherent Vice, again, and his films with Anderson — but game recognize game, and as a fellow person who needs to Do All The Things, Stiller takes the cake. And as the famously misunderstood Marie Antoinette quote goes: “Let them eat cake.” Which is also the name of an Arrested Development episode. Which is also a show Ben Stiller appeared on. I think my work here is done.

The Verdict

Chris Ryan: The key to any Upper Hand judgment is to separate your preference from your perspective. My preference is Owen Wilson. Here’s why:


That’s pretty much where I need to get in my life, so it’s hard to turn my back on it. Wilson is by far my preferred actor in this pairing. His best films are miles ahead of Stiller’s best films. His funniest movie (Wedding Crashers) is the funniest comedy either has starred in. And he’s definitely given the most interesting recent performance of the two (Inherent Vice). But Claire makes an incredible case for Stiller, right now, as a comedy benefactor, director, movie star, and actor. I’m personally not crazy about the work, and Wilson definitely holds a special place in my heart, but there’s no denying that Stiller has the Upper Hand.