Movies Like Sleepless

If you liked Sleepless, a movie directed by Manav Anil and Navin Jiji, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Happy Together (1989)
★ 5.9/10
Christopher is an ambitious college freshman, striving to become a writer. Through a computer fault he's assigned the same room as Alex, a real party freak and... a girl! He's annoyed and tries to get a different room…
2
Miller's Girl (2024)
★ 6.3/10
A talented young writer embarks on a creative odyssey when her teacher assigns a project that entangles them both.
3
American Teen (2008)
★ 6.4/10
A documentary on seniors at a high school in a small Indiana town and their various cliques.
4
How High (2001)
★ 6.4/10
Jamal and Silas, two ordinary guys who smoke something magical, pass their college entrance exams with flying colors and end up at Harvard. Ivy League ways are strange but Silas and Jamal take it in a stride -- until…
5
Lady Bird (2017)
★ 7.2/10
Lady Bird McPherson, a strong willed, deeply opinionated, artistic 17 year old comes of age in Sacramento. Her relationship with her mother and her upbringing are questioned and tested as she plans to head off to…
6
Deconstructing Harry (1997)
★ 7.2/10
Writer Harry Block draws inspiration from people he knows, and from events that happened to him, sometimes causing these people to become alienated from him as a result.
7
My Mom Jayne (2025)
★ 8/10
Through deeply personal interviews with her siblings and an examination of the photographs, letters, and belongings left behind, Mariska assembles a new portrait of her mother Jayne Mansfield, an extraordinary and…
8
Great Expectations (2012)
★ 6.4/10
Orphan Pip discovers through lawyer Mr. Jaggers that a mysterious benefactor wishes to ensure that he becomes a gentleman. Reunited with his childhood patron, Miss Havisham, and his first love, the beautiful but…
9
28 Up (1985)
★ 7.5/10
Just two years away from turning 30, participants in Michael Apted's documentary series are facing serious questions of identity and purpose, wondering whether they've found their place in the world.
10
Come See Me in the Good Light (2025)
★ 7.1/10
In an intimate and joyful story of love in the face of loss, celebrated poets Andrea Gibson and Megan Falley find strength—and unexpected hilarity—in what might be their final year together.
11
Beau Hunks (1931)
★ 6.8/10
Stan and Ollie join the French Foreign Legion after Ollie's sweetheart rejects him.
12
Some Kind of Wonderful (1987)
★ 6.8/10
Keith Nelson, an artsy high school outcast, tries to land a date with popular girl Amanda Jones with some help from his tomboy best friend, Watts. However, Watts realizes she likes Keith as more than just a friend and…
13
Do Revenge (2022)
★ 6.4/10
A dethroned queen bee at a posh private high school strikes a secret deal with an unassuming new student to enact revenge on one another’s enemies.
14
As I Was Moving Ahead Occasionally I Saw Brief Glimpses of Beauty (2000)
★ 7.8/10
A compilation of over 30 years of private home movie footage shot by Lithuanian-American avant-garde director Jonas Mekas, assembled by Mekas "purely by chance", without concern for chronological order.
15
Winter Spring Summer or Fall (2024)
★ 7.3/10
Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.
16
Geek Charming (2011)
★ 6.7/10
Film geek Josh is looking for the subject of his new documentary when a chance meeting puts the perfect star in his sights—Dylan, his school's most popular junior. But Dylan's hopes of using the film to become Blossom…
17
Chris Brown: Welcome to My Life (2017)
★ 6.4/10
This compelling Documentary moves beyond the spotlight and past the attention-grabbing headlines to give pop superstar Chris Brown a chance to tell his own story. New interviews with the international phenomenon reveal…
18
Old Boys (2018)
★ 6.6/10
In the school-set re-working of Cyrano, an awkward but imaginative pupil helps the handsome but spectacularly dim school-hero pursue the fiery daughter of a visiting French teacher.
19
The Longest Ride (2015)
★ 7.6/10
The lives of a young couple intertwine with a much older man as he reflects back on a lost love while he's trapped in an automobile crash.
20
Honor Society (2022)
★ 7.4/10
Honor is an ambitious high school senior whose sole focus is getting into Harvard, assuming she can first score the coveted recommendation from her guidance counselor, Mr. Calvin. Willing to do whatever it takes, Honor…