Dynamic Watchlist Hub: Jan 19, 2026

10 Best Movies Like Dear Sidewalk

If you loved Dear Sidewalk, 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 Dear Sidewalk.

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#1
National Lampoon's Van Wilder

National Lampoon's Van Wilder

2002★ 6.0

Why watch this? A perfect follow-up to Dear Sidewalk for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

Van Wilder has been attending college for far too many years and is scared to graduate, but Van’s father eventually realizes what is going on. When he stops paying his son's tuitio...

#2
Women of Mafia 2

Women of Mafia 2

2019★ 4.5

Why watch this? A perfect follow-up to Dear Sidewalk for fans of Drama. It captures a similar adrenaline-pumping atmosphere.

After taking control of the capital, Nanny's gang prepares for the biggest smuggling action in the history of Poland....

#3
Beautiful Boy

Beautiful Boy

2018★ 7.5

Why watch this? A perfect follow-up to Dear Sidewalk for fans of Drama. It captures a similar emotionally gripping atmosphere.

After he and his first wife separate, journalist David Sheff struggles to help their teenage son, who goes from experimenting with drugs to becoming devastatingly addicted to metha...

#4
Titanic

Titanic

1997★ 7.9

Why watch this? A perfect follow-up to Dear Sidewalk for fans of Romance & Drama. It captures a similar emotionally gripping atmosphere.

101-year-old Rose DeWitt Bukater tells the story of her life aboard the Titanic, 84 years later. A young Rose boards the ship with her mother and fiancé. Meanwhile, Jack Dawson and...

#5
Joker

Joker

2019★ 8.1

Why watch this? A perfect follow-up to Dear Sidewalk for fans of Drama. It captures a similar emotionally gripping atmosphere.

During the 1980s, a failed stand-up comedian is driven insane and turns to a life of crime and chaos in Gotham City while becoming an infamous psychopathic crime figure....

#6
Harry Potter and the Prisoner of Azkaban

Harry Potter and the Prisoner of Azkaban

2004★ 8.0

Why watch this? A perfect follow-up to Dear Sidewalk for fans of Adventure. It captures a similar compelling atmosphere.

Year three at Hogwarts means new fun and challenges as Harry learns the delicate art of approaching a Hippogriff, transforming shape-shifting Boggarts into hilarity and even turnin...