20. She’s Funny That Way (2014)
This was a late-period Peter Bogdanovich film, a screwball spin on Ernst Lubitsch, that had Imogen Poots as the golden-hearted sex worker trying to break into show business. She walks into an audition in front of a big-shot Broadway director and realises he is the man to whose Manhattan hotel room she had gone the night before. And that director is played by Owen Wilson, with that good-natured, halting Texas drawl which was to feature to some degree in all of his performances. He is a pretty bland nice guy here – a default mode he sometimes goes into a bit too easily.
19. The Big Bounce (2004)
Genre veteran and Roger Corman associate George Armitage (who made Grosse Pointe Blank) directed this aimless crime comedy from Elmore Leonard’s novel of the same name. Wilson takes the starring role, which in the previous adaptation of 1969 had belonged to Ryan O’Neal – and there are similarities between them, two eye-candy leading men who can so easily become opaque. Wilson is the Hawaii beach bum and grifter who gets mixed up in a series of capers orchestrated by various shady types, including Morgan Freeman’s dodgy judge. Here he is coasting.
18. Meet the Fockers (2004)
Apart from director Wes Anderson, the one figure whose name has been yoked to Wilson’s was Ben Stiller; Stiller’s gift for dark satire, discomfort and ironised self-awareness made a nice foil to Wilson’s sunny openness. Meet the Fockers is the sequel to the cringe-comedy Meet the Parents, in which Stiller’s girlfriend’s insufferably attractive and charismatic ex-boyfriend (Wilson) turns up, again briefly, playing a New Age interfaith priest.
17. Shanghai Noon (2000)
As so often in Jackie Chan’s career, Hollywood patronised him by insisting on a pairing with a more obvious partner. It was Wilson in this wacky spoof western, whose title is a pun on the famous western High Noon. The idea is that in 1881 Chan has to rescue a princess who has been spirited away to the lawless wild west, and there he is to team up with a laid-back, supercool outlaw: Roy O’Bannon, played by Wilson. The film sends up Butch Cassidy and the Sundance Kid at one stage, and certainly Wilson has something of Robert Redford about him – but he is maybe too mischievous and comedy-oriented to have had Redford’s career.
16. Starsky & Hutch (2004)
Wilson was heard chatting about the TV classic Starsky & Hutch as far back as Wes Anderson’s early short film Bottle Rocket. But in the mid-00s he and Stiller were the only possible contenders to play the two iconic 70s TV dreamboat cops: he was the blond Ken “Hutch” Hutchinson (originally David Soul) opposite Stiller’s David Starsky (originally Paul Michael Glaser). Wilson amusingly plays up the gay subtext to his bromantic relationship with Starsky, but the actual irony and mockery is kept under control in both his performance and the film itself in favour of a reasonably straightforward action comedy.
15. Behind Enemy Lines (2001)
A unique example of Wilson playing it entirely straight in an action movie based on real events, opposite a similarly hatchet-faced Gene Hackman (with whom he was in the same year to co-star in Wes Anderson’s The Royal Tenenbaums). For all that there is something weird in seeing him play such a serious role, he does a perfectly good job as the US navy flight officer shot down behind enemy lines in the 90s during the Bosnian war, and there are some exciting action set pieces. Perhaps this is the film to ponder one of the most distinctive things about Wilson: that broken nose of his, hinting at some violence in his past which never surfaces in his amiable screen persona.
14. The Darjeeling Limited (2007)
Wilson plays one of three brothers, with Jason Schwartzman and Adrien Brody, travelling across India to heal emotional wounds following the death of their father, on a train that, zanily, gets lost. Wilson’s face is covered with bandages, as if to make those emotional wounds manifest, and at one stage he tries to remove them – a process that is too painful. It is a moment that, by accident or design, gestures at the emotional pain that Wilson himself – with a history of depression – has been known to suffer.
13. The Grand Budapest Hotel (2014)
This film is often hailed as Wes Anderson’s best – and so it might be, although Wilson’s contribution is relatively low-key. He is Monsieur Chuck, a fellow concierge and professional comrade of Ralph Fiennes’s Monsieur Gustave, the noted concierge and eminence grise of the Grand Budapest Hotel itself. M Chuck is a member of the Society of the Crossed Keys, along with M Ivan, played by Bill Murray. It is a quick ensemble turn, but Wilson adds to the gaiety.
12. Inherent Vice (2014)
Here is the other Anderson that Wilson has worked for – Paul Thomas Anderson, and in some ways it’s a surprise that Wilson has not become one of his repertory stalwarts as well. In this vivid version of the Thomas Pynchon novel, Wilson plays Coy Harlingen, one of the minor characters skulking in the dense, semi-serious thickets of mystery that surround the action. He is a lowlife informant who has gone missing, and whose addict wife (Jena Malone) employs private detective Doc Sportello (Joaquin Phoenix) to go looking for him. The film taps into a (marginally) darker side to Wilson.
11. Bottle Rocket (1996)
Wilson made his debut, along with his brother Luke, in this hugely loved, quirky and faintly slacker-ish film from the 90s era of Linklater and Tarantino. It was developed from an earlier short film, and Anderson’s trademarks were not yet really in evidence. Wilson – with short hair, rather like that of a member of the US Marine Corps, which the actor had been thinking of joining – plays a young guy trying to get his friend (Luke) sprung from psychiatric hospital so that they can carry out a series of heists. Again, this film hints very obliquely at real sadness and pain.
10. Marley & Me (2008)
This date-movie weepie heartwarmer, however unbearable, undoubtedly has a major position in the Wilson canon. He plays John Grogan, a journalist married to a woman played by his nearest female movie-actor equivalent, Jennifer Aniston. His professional and personal life is redeemed by writing a regular column about his relationship with his dog, an adorable labrador called Marley who is with him during all his personal travails, until of course Marley gets sick and his time in this vale of tears comes to an end. Wilson’s tearful final speech to Marley at the vet’s (“You’re a great dog …!”) made demands of him as an actor as no other film did.
9. You, Me and Dupree (2006)
Wilson’s wedding comedy is likable and funny, and deserves to be remembered a bit more than it is. He goes into his good-natured wackiness mode in this three’s-a-crowd caper, in which he plays a goofy loser called Dupree who gets in between a married couple, a bit like Bill Murray in What About Bob?. Matt Dillon and Kate Hudson play two newlyweds who rashly feel sorry for Dupree, Carl’s best man, who has just lost his home and job. They let him crash with them – with awful results.
8. Wedding Crashers (2005)
The sheer high-concept outrageousness of this comedy – very much a product of the frat-pack 00s – has kept it a fan favourite, and there are real laughs. Wilson is perfectly positioned alongside the grinning figure of Vince Vaughn. They play two commitment-phobe guys who are running an appalling scam: they gatecrash weddings to zero in on attractive single women who are feeling vulnerable because they are not yet married and sentimentally believe that a man they meet at a wedding must be The One. Of course, it is nice-guy Wilson who really does fall for someone there, and he nicely plays both the cynicism and then the emotional life lesson.
7. Cars (2006)
Wilson’s vocal performance in this Pixar animation is arguably the nearest he ever got to a conventional action-adventure lead – it’s not my favourite Pixar but, undoubtedly, he flavoured it with his winning personality. He is Lightning McQueen, a feisty, headstrong young sports car who is dead set on winning the prestigious Piston cup on his very first outing. But events conspire to strand him in the middle of the desert, where he learns lessons in humility from an old 50s auto voiced by Paul Newman. In some ways, the beaming face of Lightning McQueen personifies the perky, upbeat side of Wilson’s persona.
6. The Royal Tenenbaums (2001)
Wilson has a supporting but very distinctive role here in this great Wes Anderson film, as someone who is not part of the dysfunctional Tenenbaum family, presided over by Gene Hackman’s haughty paterfamilias. As neighbour Eli Cash, he affects a Stetson and writes sub-Larry McMurtry western novels, coolly affronted when critics fail to call him a genius; at one point, he distractedly walks out of a TV interview that had alluded to the relative failure of an early work. He is the best friend of tortured tennis champ Richie Tenenbaum, played by Luke Wilson, a relationship that revives something of the Bottle Rocket dynamic and creates an agonised problem when Richie reveals himself to be in love with his adopted sister Margot (Gwyneth Paltrow), who is dating Eli.
5. Meet the Parents (2000)
A tremendously good comic turn is what Wilson delivers in this broad comedy, remade from a 90s indie. Ben Stiller plays a beta-male with the name Gaylord “Greg” Focker, whose girlfriend Pam (Teri Polo) brings him home to meet her parents, the dad being a terrifying ex-CIA man amusingly played by Robert De Niro. Greg is horribly humiliated throughout the visit, but never more than by meeting Pam’s ex-boyfriend Kevin, wonderfully played by Wilson: a mega-wealthy alpha male, inspired by Jesus to become a carpenter, who can’t quite grasp that Greg’s job as a nurse isn’t “volunteer” work he’s selflessly doing away from what must surely be proper employment.
4. Fantastic Mr Fox (2009)
One of Anderson’s most audacious and yet inspired moves was this Americanisation of Roald Dahl’s story Fantastic Mr Fox as a stop-motion animation in which all the leads were voiced by Americans and all the kids play a baseball-type sport called “whack bat”. This is taught by Coach Skip, laconically voiced by Wilson, who, with his descriptions of whack bat’s arcane mysteries, beguilingly conveys how strange it all is, and how strange the whole story is, all with a light touch.
3. The Life Aquatic with Steve Zissou (2004)
It may not be Anderson’s best film but Wilson has a very touching role as Ned, a young guy who hero-worships the Jacques Cousteau-type oceanographer Steve Zissou, played by Bill Murray. Ned leaves his job as an airline pilot to volunteer with Steve’s crew, and even bankrolls the next Zissou documentary – the implication being that Ned is in fact Steve’s son. There is a lot of deadpan comedy along the way, but Murray and Wilson together get an unexpectedly exciting and then affecting death scene in the helicopter they’re piloting.
2. Midnight in Paris (2011)
Wilson carries an old-fashioned romantic lead in Woody Allen’s minor but still relatively amusing fantasy-comedy (certainly more satisfyingly than in Bogdanovich’s comparable film She’s Funny That Way). He is a disillusioned Hollywood screenwriter who comes to Paris for a break with his fiancee (Rachel McAdams) and, pining for the belle époque, gets into a carriage that carries him back in time to the city of Hemingway, Fitzgerald and Picasso; he even has a dalliance with Picasso’s mistress, played by Marion Cotillard. Wilson plays the role with absolutely the right kind of throwaway fun: he is bemused and excited, bobbing along on the action like a cork on water.
1. Zoolander (2001)
So hot right now! Wilson’s masterpiece has to be his portrayal of the overwhelmingly handsome and compellingly modish male model with the unimprovable name of Hansel, the young contender who snatches the male model crown from the head of pouting Derek Zoolander, played by Ben Stiller. The montage scene at the Male Model of the Year awards, showing Hansel’s achievements in modelling, is a glorious showcase for Wilson’s actual, overwhelming handsomeness. To an off-camera interviewer, Hansel establishes his sensitivity and emotional intelligence by murmuring, “Richard Gere’s a real hero of mine … and Sting.” And his “walk-off” contest with Zoolander, judged by David Bowie, is another iconic moment.