The “quintessential ’90s movie”, according to Jake Gyllenhaal
The 2020s have so far been the decade that brought the 1990s back in a big way, from fashion to music to movies; some of it was great, some of it wasn’t, but it was certainly a good ten years for films, as Jake Gyllenhaal likes to point out.
It was in the ‘90s that Gyllenhaal began his career as an actor, on the Billy Crystal comedy City Slickers in fact, a movie that isn’t bad at all, but is probably notable for being the first example of a character on screen talking badly about another character, and then going ‘he’s behind me isn’t he’, which has since been done approximately 10,000 times.
Anyway, Gyllenhaal played a kid in that successful film, but it didn’t lead to immediate fame; he had school to finish for one thing. Once he was done with it, though, he very quickly began to make a name for himself in Hollywood, no doubt aided to some degree by virtue of his director father, his screenwriter mother, and his older sister Maggie, who was already an actor.
Nevertheless, by the end of the decade, Gyllenhaal had made two further films, Homegrown, a dark thriller starring Billy Bob Thornton and 1999’s October Sky, which was his first lead role, opposite Jurassic Park’s Laura Dern. It was very well received, and Gyllenhaal, who had yet to turn 20, was seen as a genuine talent, with the drama helping him to land the lead in 2001’s Donnie Darko, a massive hit.
His own taste in movies is clearly reflected in the fact that he came of age in the ‘90s, and he especially singles out a movie from Cameron Crowe that did huge numbers for Tom Cruise right in the middle of it.
Speaking to Rotten Tomatoes, Gyllenhaal said of 1995’s Jerry Maguire: “It’s just something I can never turn off whenever it’s on the television, and I think that has a power of its own. I feel like it’s a quintessential ’90s movie. You know what I mean? I would actually put Jerry Maguire and Fast Times at Ridgemont High right up there with each other, in the same spot.”
Directed by Cameron Crowe, who also wrote the screenplay for ‘80s staple Fast Times, Jerry Maguire was the sports agent comedy drama that spawned several catchphrases on its release, most famously Cruise’s cry of “Show me the money!”. Co-starring Cuba Gooding Jr and Rene Zellweger, it was a box office success and a favourite with critics, getting nominated for five Oscars, Gooding Jr winning for ‘Best Supporting Actor’, and it made almost $300million at cinemas.
Meanwhile, after a somewhat shaky start to 2026 with an appearance in his sister’s flop horror The Bride!, and a Guy Ritchie action flick In the Grey, which came and went with whatever the opposite of fanfare is, Gyllenhaal is now working on a raft of different movie projects due for release over the next couple of years.
Those include a sequel to his surprise reboot hit Road House, plus an adaptation of the Tom Clancy-inspired video game The Division, and an M Night Shyamalan thriller called Remain, which isn’t about Brexit, co-written with The Notebook’s Nicholas Sparks.
