These are jokes based on the titles of these movies. If somebody can suggest a better joke for a certain title (or a continuation of the same joke), I will replace it. Best joke wins.
(Joe Newman also contributed to this list. Thanks, Joe)
City Slickers: Jake stars as Billy Crystal’s son in this powerful drama about a man who salts streets for a living until a group of rambunctious hockey players comes to town.
Josh and S.A.M.: Josh Sullivan (Gyllenhaal) creates the Sullivan acronym machine (S.A.M.), much to the annoyance of his entire family.
A Dangerous Woman: Debra Winger learns to breathe fire after eating too many spicy wings. Gyllenhaal plays her concerned son.
Homegrown: tense drama about Billy Bob Thornton growing houses from Magic beans. Gyllenhaal plays the elf who helps him harvest the beans.
October Sky: Pollution from the candy corn factory turns the sky bright orange on Halloween night. Jake Gyllenhaal plays one of the workers at the factory, who hopes to one day manufacture Rocket pops.
Donnie Darko: Tired of wearing black clothing, Donnie Darko decides to buy some white socks.
Bubble Boy: Gyllenhaal stars as a guy who loves blowing bubbles. Unfortunately, the world is facing a shortage of the resources to make bubble wands.
Lovely and Amazing: Adaptation of one of Barry Manilow’ unreleased songs.
Highway: Gyllenhaal and Jared Leto smoke a joint in a traffic jam.
The Good Girl: Working in a Lingerie store, Jake plays a young tortured writer who goes undercover in drag to earn the cutthroat department store’s most coveted title: “The Good Girl.”
Moonlight Mile: Gyllenhaal plays a long-distance runner by day and a werewolf by night.
The Day After Tomorrow: In this sequel to Groundhog Day, Gyllenhaal keeps waking up the day after tomorrow. Dennis Quaid is also in this movie for some reason.
Brokeback Mountain: Gyllenhaal goes to chiropractor Heath Ledger in Denver. Rocky Mountain High is played during every massage scene.
Proof: Gyllenhaal plays a magician who cannot say the word “poof” properly. Gwyneth Paltrow and Anthony Hopkins play the doctors trying to help him.
Jarhead: Inspired by Castaway. Gyllenhaal finds a head in a jar (played by Tom Hanks) in the middle of the desert and takes to calling it Jarhead. Over the course of the movie, they become best friends and learn something about each other.
Zodiac: Docudrama that details how Ted Cruz (played by Gyllenhaal) transitioned from infamous serial killer to national politician.
Rendition: Gyllenhaal travels across the country, covering all the greatest hits with his soulful renditions.
Brothers: Known as Eskimo Brothers in Canada, it follows two brothers (Gyllenhaal and Tobey Maguire) as they race across the tundra to win the love of a good woman (Natalie Portman). Was condemned by the Inuit community.
Prince of Persia: Sands of Time – Prince gets a gig performing at the Persia, a new casino in Las Vegas. He gets a new hourglass delivered to him by Gyllenhaal.
Love & Other Drugs: Scientists isolate the pheromone that causes love and inject it into heartbroken slam poet and lab rat Gyllenhaal. Sold with the tagline “Better than Viagra.”
Source Code: Gyllenhaal stars as a computer who falls in love with a scientist played by Scarlett Johansson.
End of Watch: Follows Gyllenhaal’s race against time to save his dying stopwatch.
Prisoners: Sequel to The Wolf of Wall Street. Jordan Belfort (Gyllenhaal) has to help Tommy Chong hide his pot from the guards.
Enemy: Enemy (Gyllenhaal) considers changing his name to find a friend.
Nightcrawler: In this Marvel comic book adaptation, Jake Gyllenhaal stars as Kurt Wagner, a blue-skinned man with a tail gifted with teleportation, and follows his humble beginning as circus freak to becoming a full-fledged member of the X-Men. He also sues the blue man group and Avatar for copyright infringement.
Accidental Love: Jennifer Biel stars as an insurance agent who falls for the accident-prone Gyllenhaal. Climax takes place in a Banana Peel Factory.
Southpaw: Jake Gyllenhaal picks up a cursed monkey’s paw in New Orleans.
Everest: Documentary about Gyllenhaal planning to climb Everest, only to settle on going skiing instead.
Demolition: Gyllenhaal plays a demolition derby driver who must overcome his fear of destroying cars to win the big match.
Nocturnal Animals: Disney Pixar film. Gyllenhaal voices a bat who’s in love with a red-eyed tree frog played by Amy Adams.
Life: Adaptation of the Hasbro board game The Game of Life. Gyllenhaal rolls a six and gets put in jail with Ryan Reynolds.
Okja: Gyllenhaal can’t decide what to name his pet turtle.
Stronger: Gyllenhaal plays steroids in this animated family film about Lance Armstrong.
Wildlife: Gyllenhaal plays Fred Flinstone, a hunter gatherer who rides around on his pet T-rex searching for food for his family in this serious drama. Disregarded by the scientific community.