Watch Trippin' (1999): stream Trippin' (1999) on Apple TV+, or rent on Apple TV+ or Fandango At Home. Compare all streaming options for this movie on WhereCanIWatch.tv.
Trippin'
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You can stream Trippin' (1999) on Apple TV+ with a subscription, rent on Apple TV+, or buy on Apple TV+.
Greg is near the end of his senior year in high school, wanting to go to the prom, eyeing Cinny (the school's beauty with brains) from afar, and regularly trippin', daydreaming about being a big success as a poet, a student, a lover. His mom wants him to apply to colleges, but Greg hasn't a clue. One of his teachers, Mr. Shapic, tries to inspire him, too. He finally figures out he can get close to Cinny if he asks her for help with college applications. But friendship isn't enough, he wants romance and a prom date. So, he tells a few lies and, for awhile, it seems to be working. Then, things fall apart and Greg has to figure out how to put the trippin aside and get real.
A daydreaming poet struggles to balance his lofty romantic fantasies with the looming pressure of college applications and senior year reality. This urban comedy captures the awkward, high-energy chaos of trying to secure the perfect prom date while finding your footing in the world.
Director
David Raynr
Cast
Deon Richmond, Donald Faison, Guy Torry, Maia Campbell, Anthony Anderson, Aloma Wright, Natashia Williams, Stoney Jackson, Countess Vaughn, Shondrella Avery
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5 options ranked by value · 🇺🇸 United States
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Last verified 9 days ago
Trippin'
You can stream Trippin' (1999) on Apple TV+ with a subscription, rent on Apple TV+, or buy on Apple TV+.
IMDb
4.7/10
RT Critics
19%
Director
David Raynr
Cast
Deon Richmond, Donald Faison, Guy Torry, Maia Campbell, Anthony Anderson, Aloma Wright, Natashia Williams, Stoney Jackson, Countess Vaughn, Shondrella Avery
5 options ranked by value · 🇺🇸 United States
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high school · prom
Trippin' is streaming on Apple TV+. Rent Trippin' on Apple TV+. Rent Trippin' on Fandango At Home. Buy Trippin' on Apple TV+. Buy Trippin' on Fandango At Home. Trippin' is not currently available on Netflix, Hulu, Max, Disney+, Prime Video. Availability last verified July 6, 2026.