Dynamic Watchlist Hub: Apr 15, 2026

10 Best Movies Like April May '99

If you loved April May '99, 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 April May '99.

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#1
The Sisterhood of the Traveling Pants 2

The Sisterhood of the Traveling Pants 2

2008★ 6.3

Why watch this? A perfect follow-up to April May '99 for fans of Drama. It captures a similar light-hearted atmosphere.

Four young women continue the journey toward adulthood that began with "The Sisterhood of the Traveling Pants." Now three years later, these lifelong friends embark on separate pat...

#2
People We Meet on Vacation

People We Meet on Vacation

2026★ 7.0

Why watch this? A perfect follow-up to April May '99 for fans of Drama. It captures a similar light-hearted atmosphere.

Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match....

#3
The Last Song

The Last Song

2010★ 7.2

Why watch this? A perfect follow-up to April May '99 for fans of Drama. It captures a similar emotionally gripping atmosphere.

A drama centered on a rebellious girl who is sent to a Southern beach town for the summer to stay with her father. Through their mutual love of music, the estranged duo learn to re...

#4
The Sisterhood of the Traveling Pants

The Sisterhood of the Traveling Pants

2005★ 6.5

Why watch this? A perfect follow-up to April May '99 for fans of Drama. It captures a similar light-hearted atmosphere.

Four best friends (Tibby, Lena, Carmen & Bridget) who buy a mysterious pair of pants that fits each of them, despite their differing sizes, and makes whoever wears them feel fa...

#5
The Way Way Back

The Way Way Back

2013★ 7.1

Why watch this? A perfect follow-up to April May '99 for fans of Drama. It captures a similar light-hearted atmosphere.

Shy 14-year-old Duncan goes on summer vacation with his mother, her overbearing boyfriend, and her boyfriend's daughter. Having a rough time fitting in, Duncan finds an unexpected ...

#6
Ana

Ana

2020★ 6.3

Why watch this? A perfect follow-up to April May '99 for fans of Drama. It captures a similar light-hearted atmosphere.

Ana meets Rafa in a chance encounter and they embark on a road trip to try and save him from bankruptcy, or worse....

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