Crazy, Stupid, Love (2011) ›

One night, he encounters Jacob Palmer (Ryan Gosling), a smooth, impeccably dressed womanizer who holds court at a trendy LA nightclub. Annoyed by Cal's pathetic attempts to get drunk, Jacob takes him under his wing. Over a montage of makeovers, wingman sessions, and cynical lessons ("Be better than the Gap"), Jacob transforms Cal into a suave, one-night-stand machine, complete with new clothes, new confidence, and a rotating cast of anonymous women.

Second, Cal's 13-year-old son, Robbie (Jonah Bobo), is hopelessly in love with his 17-year-old babysitter, Jessica (Analeigh Tipton), who is herself secretly, desperately in love with the older Cal. This cringey, earnest subplot mirrors the film's central theme: love, in all its forms, is inherently crazy and stupid. crazy, stupid, love (2011)

The film is frequently cited as a high-water mark for the "post-modern" romantic comedy—one that acknowledges genre clichés while subverting them. It avoided the saccharine predictability of many rom-coms, earning a Certified Fresh rating of 79% on Rotten Tomatoes. The consensus reads: "It's far more smart than its title suggests, and features a multi-generational cast firing on all cylinders." One night, he encounters Jacob Palmer (Ryan Gosling),