23 romantic comedies worth watching this Valentine's Day

Tootsie (1982)

Dustin Hoffman’s out of work actor manages to find a soap opera role – by pretending to be a woman called Dorothy Michaels. All sorts of romantic chaos ensues as Hoffman falls for his female co-star and several men fall for Dorothy, but what could so easily end up as lazy, unfunny farce becomes gold due to Hoffman’s superb performance (for which he was Oscar nominated; his co-star Jessica Lange won, however).

Bringing Up Baby (1938)

Howard Hawks’ absurd screwball comedy is certainly of its time, but retains a healthy dose of charm through the inspired casting of Cary Grant and particularly Katherine Hepburn, who play two decidedly unmatched characters who end up falling for each other after a series of madcap antics concerning leopards, dogs and a travelling circus. It was remade – with less than impressive results – in 1987 as Who’s That Girl? (yes, the Madonna movie).

High Fidelity (2000)

This adaptation of Nick Hornby’s novel may trade London for Chicago and have the slightly-too-goodlooking John Cusack as its music-obsessed, commitment-phobic leading man, but Stephen Frears manages to retain the book’s heart and themes, specifically: when is it time to grow up? We suspect there’s something in there with which most men of a certain age can identify. Cusack, to his credit, co-wrote the screenplay.

(500) Days of Summer (2009)

Joseph Gordon-Levitt and Zooey Deschanel are the quirksome couple in this offbeat romcom, which riffed nicely on the latter’s status as a certain kind of guy’s “manic pixie dream girl” by having her play one. And it goes against the romcom grain by ending on a downer and reminding us that life isn’t a movie (ironic we know) and sometimes your dream girl doesn’t find herself irrevocably changed by your unique charms after 90 minutes. Happy Valentine's Day!