I had a sneaking suspicion that I preferred Ben Stiller’s ‘unpopular’ films to his more popularist outings, and after watching recently The Secret Life of Walter Mitty (2013), it was confirmed. That film, along with Greenberg (2006) and While We’re Young (2015) make a sort of loose trilogy of dreamer/loser films which I relate to: in Greenberg he’s a drifter who returns to L.A. to sort his life out; in While We’re Young he’s a failed documentary filmmaker having a mid-life crisis; The Secret Life of Walter Mitty finds his job in jeopardy after a company takeover. At least two of these things have happened to me in recent years.

It’s so random when films (like music) directly speak to you. They don’t have to be good in any way; they can even be very bad, but something about them sparks a feeling, thought or memory that has meaning.

The three Ben Stiller films all have darker humour and more realism than his more mainstream box-office hits such as Zoolander, Night at the Museum or Meet the Parents. Even though he plays a similar character in most of his films, his popular, gross-out comedies involve slapstick humour and have more mass appeal. Mainly, though, Greenberg, The Secret Life of Walter Mitty and While We’re Young, well, they just aren’t as funny (though I found them hilarious!), and the characters he plays mostly aren’t very likeable.

In Greenberg, with hip credentials in the form of music by James Murphy, formerly of LCD Soundsystem, Stiller plays the eponymous curmudgeon Roger Greenberg, a carpenter just back in L.A. after a nervous breakdown whilst living in New York. His character isn’t that nice; he doesn’t know what to do with his life; he treats people pretty badly (though still gets to shag Greta Gerwig). There’s a lack of plot and cynicism to the film I quite enjoyed.

The Secret Life of Walter Mitty, based on the 1939 short story by James Thurber, and has since entered into common language as an ineffectual person who daydreams, stars Stiller as Walter Mitty, a negative assets manager on Life magazine. The magazine is about to be taken over by a corporation, Mitty’s job is in jeopardy and he has to track down the final print edition cover image taken by photojournalist Sean O’Connell (Sean Penn), the negative of which has gone missing.

His daydreams of adventure and daring become his reality when he tracks down O’Connell by flying to Greenland, jumping from a helicopter into shark-infested waters, skateboarding to Iceland and fleeing an erupting volcano. He finally tracks down O’Connell in the Himalayas. As it turns out, the negative was in a wallet O’Connell gave Mitty at the start of the film. The final scene has Mitty and co-worker/girlfriend Cheryl Melhoff (Kristen Wiig) seeing the final Life cover at a news stall, with a black and white picture of Mitty sitting outside his office building reading a copy of Life. The irony of Mitty working for Life magazine, when he didn’t actually have one, cannot have been lost on him, but by the end of the film, he’s finally lived, though got sacked, and, well, sits in coffee shops on his laptop applying for jobs (this is the problem with travelling – you have all these amazing experiences, come back home, then end up in a soulless office, wondering how it happened). God, that’s almost as bad as actually having a job.

(The first five minutes are actually the funniest, with Walter at home on his laptop trying to contact co-worker Cheryl on a dating website, debating over and over whether to press send, eventually plucking up courage, then realising his connection is down.)

While We’re Young (one of my films of the year last year, and the Guardian’s), has Josh (Stiller) and Naomi Watts (Cornelia – has anyone actually been named that in the last hundred years?) as a couple in their forties who have tried and failed to have children. Stiller is a struggling documentary film-maker who has been working on the same film for years. The release from the frustration of their relationship comes in the form of two young freewheeling hipsters who befriend the older couple. At first Jamie (Adam Driver), an aspiring film-maker, looks up to Josh and becomes his protégé, but soon Josh is embarrassingly emulating his hipster buddy with bikes, hats, manual typewriters, vinyl records and other hipster memorabilia. Then things turn darker altogether.

All three films fared badly at the box office, due to their dark tone, unsympathetic characters and lack of a narrative (apart from Walter Mitty, which is full of plot and pretty light, but touches on important issues). One star DVD reviews on Amazon testify to their unpopularity: While We're Young: “rubish” [their spelling]; “crap”; “dull”; Greenberg: “tedious”; “boring”; “pointless”; The Secret Life of Walter Mitty: “boring”; “tedious”; “waste of money”.

Partly because he’s roughly the same age as me, like Ethan Hawke in the Before Sunrise trilogy, I feel as if I’ve grown up with Ben Stiller. I wouldn't say I’m a huge fan, but he’s got a funny face and his look of “quiet desperation” (The Guardian’s phrase) strikes a chord with me.

Previously on Barnflakes
Sex and the City 2 Vs Greenberg
James Murphy: the Emperor’s Old Clothes
Busy being’ busy
Film dreams