David Thomson on Owen Wilson

Easygoing exterior ... Owen Wilson. Photograph: Matthew Simmons/PA

It's a long time since Woody Allen has had a success to match Midnight in Paris. In fact he never has. Opening in the US on 22 May, at a cost of around $30m, it has already grossed in the region of $40m. Is that just Paris and "midnight"? Is it the amiable, lackadaisical air of the very light film? (If it wasn't on a string it might fly away.) Or is it Owen Wilson? He plays the screenwriter hoping to be more respectable who gets to meet Scott, Zelda, Hem and Gertrude Stein when a splendid antique car comes by on a back street at midnight? It helps a lot that Wilson isn't Woody. Allen cast himself as his romantic lead way too long, and it's refreshing to see Wilson – that rarity among male stars now in that he's a true blond – who looks smart enough to have written something, but anxious enough to be disappointed with it.

Midnight in ParisProduction year: 2011Country: Rest of the worldRuntime: 100 minsDirectors: Woody AllenCast: Adrien Brody, Carla Bruni, Kathy Bates, Marion Cotillard, Michael Sheen, Owen Wilson, Rachel McAdams, Tom HiddlestonMore on this film

The anxiety is more than an impression. The young actor-writer has had significant bouts with depression, and those can hardly be attributed to his career going badly. He has had much bigger hits than Midnight in Paris. The Jackie Chan vehicle, Shanghai Noon (2000), in which he co-starred, was a hit. Wedding Crashers (2005), in which he starred with Vince Vaughn, grossed more than $200m in the US, while Marley & Me (2008), in which he played opposite Jennifer Aniston and a dog, has grossed close to a quarter of a billion dollars worldwide. Perhaps Wilson was the least essential of its three stars, but the public is comfortable with him and his natural, unforced sense of humour.

So the easygoing exterior may be masking a lot. The key to Wilson's work so far is not the big hits. It's the importance of creative friendship and alliance. So Wilson is joined at the hip with director Wes Anderson. Wilson acted in and co-wrote Bottle Rocket (1996), he and Anderson wrote Rushmore (1998) together and then did the same on The Royal Tenenbaums (2001), for which they got an Oscar nomination for original screenplay (plus Wilson played the druggie friend of the family in love with Gwyneth Paltrow and rewriting classics of the west). Since that, he has acted in other Anderson pictures – The Life Aquatic With Steve Zissou (2004), The Darjeeling Limited (2007) and as the voice of Coach Skip in Fantastic Mr Fox (2009).

The other important association is with the actor-director Ben Stiller. They worked together for the first time when Wilson played a part in the Jim Carrey film The Cable Guy (1996), directed by Stiller. They then acted together in the drug-ridden Permanent Midnight (1998), one of Wilson's few serious dramatic roles. They have also worked together in Zoolander, Starsky & Hutch, the Fockers films and Night at the Museum pictures.

It may depend on your mood, or your sense of life, as to whether or not you find that record depressing. Wilson has not had a writing credit since The Royal Tenenbaums (which doesn't mean he hasn't put pen to paper). So Allen's use of him in Midnight in Paris may not be incidental, and Wilson may have felt desperate occasionally over the comedies he was slotted into, and their steady success.

He did play a serial killer in The Minus Man (1999), and he was creepy and disturbing. Gene Hackman (who had been with him in Tenenbaums) got him to play the airman shot down Behind Enemy Lines (2001) in Bosnia, and Wilson seemed capable of fear   and desperation.

He keeps very busy and has done voices in the Cars films. Owen Wilson is reliable at the box office, funny, engaging and passably romantic. But suppose at 42 that he feels those strains running out and wonders if there might not be a grand challenge for him somewhere, a story that gets him to cut his hair and have the friendly grin wiped off his face. What's the point, you say, if your films have grossed over $2bn? But this guy apparently tried to kill himself and the writer in Midnight in Paris who seems to have the girl, the lifestyle and the confidence needs something else. It's not the craziest idea that Owen Wilson could try playing Scott Fitzgerald – good-looking, talented, well-married, a man of the moment, but believing very little of it.

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