Dynamic Watchlist Hub: Jan 26, 2026

10 Best Movies Like A High Wind in Jamaica

If you loved A High Wind in Jamaica, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for A High Wind in Jamaica.

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#1
Baby Boom

Baby Boom

1987★ 6.4

Why watch this? A perfect follow-up to A High Wind in Jamaica for fans of Drama. It captures a similar light-hearted atmosphere.

J.C. Wiatt is a talented and ambitious New York City career woman who is married to her job and working towards partner at her firm. She has a live-in relationship with Steven, a s...

#2
Motorama

Motorama

1991★ 6.5

Why watch this? A perfect follow-up to A High Wind in Jamaica for fans of Adventure. It captures a similar light-hearted atmosphere.

A ten year old boy gets tired of life with abusive parents and cashes in his piggy bank and steals a Mustang. He rides off into a surreal America playing "Motorama," a game sponsor...

#3
The Last Starfighter

The Last Starfighter

1984★ 6.6

Why watch this? A perfect follow-up to A High Wind in Jamaica for fans of Adventure. It captures a similar adrenaline-pumping atmosphere.

Video game expert Alex Rogan finds himself transported to another planet after conquering the video game The Last Starfighter, only to find out it was just a test. He was recruited...

#4
Leave 'Em Laughing

Leave 'Em Laughing

1928★ 5.9

Why watch this? A perfect follow-up to A High Wind in Jamaica for fans of Comedy. It captures a similar light-hearted atmosphere.

Stan complains of a toothache and he and Ollie visit the dentist. Ollie gets his teeth pulled by mistake. Under the influence of laughing gas, they leave and cause much commotion o...

#5
Hilda Crane

Hilda Crane

1956★ 7.2

Why watch this? A perfect follow-up to A High Wind in Jamaica for fans of Drama. It captures a similar emotionally gripping atmosphere.

After two failed marriages, a disillusioned woman returns to her hometown to start life anew....

#6
Wilson

Wilson

1944★ 5.5

Why watch this? A perfect follow-up to A High Wind in Jamaica for fans of Drama. It captures a similar emotionally gripping atmosphere.

The political career of Woodrow Wilson is chronicled, beginning with his decision to leave his post at Princeton to run for Governor of New Jersey, and his subsequent ascent to the...