Movies Like Kaptn Oskar

If you liked Kaptn Oskar (2013), a comedy and drama movie directed by Tom Lass, 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
Delirious (2007)
★ 6.3/10Also comedy and drama
Les, a small-time celebrity photographer desperate to make it big, befriends Toby, a homeless young man with no direction except a vague desire to become an actor. When by chance, Toby becomes romantically involved…
2
Numb (2007)
★ 5.9/10Also comedy and drama
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel…
3
You Will Meet a Tall Dark Stranger (2010)
★ 5.9/10Also comedy and drama
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling…
4
Camille (2008)
★ 6.2/10Also comedy and drama
A twisted honeymoon adventure about a young couple on their way to Niagara Falls.
5
Dreamfactory (2019)
★ 7.3/10Also drama and comedy
A romantic drama set in 1961 that follows a young studio extra's ambitious efforts to reunite with the French girl he loves after being separated by the construction of the Berlin Wall.
6
Young People Fucking (2007)
★ 5.9/10Also comedy and drama
On a Tuesday night, five couples have separate sexual adventures. Matt and Kris, friends for years, want to have an only-once, no-strings good time. Abby and Andrew, married, celebrate his birthday, but it's marred by…
7
Enemies, a Love Story (1989)
★ 6.2/10Also comedy and drama
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
8
Is This Thing On? (2025)
★ 6.6/10Also comedy and drama
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to…
9
XX/XY (2002)
★ 6/10Also drama and comedy
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
10
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
11
It's Just a Phase, Honeybunny (2021)
★ 6.2/10Also comedy and drama
The successful writer Paul and the sought-after voice actress Emilia were always considered to be the absolute dream couple by friends: Harmonious, happy, successful, with three charming children named Bo, Marie and…
12
The Best You Can (2025)
★ 7/10Also comedy and romance
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside…
13
Cyrus (2010)
★ 5.9/10Also comedy and drama
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before…
14
Edges of the Lord (2001)
★ 6.4/10Also comedy and drama
A 12-year-old Jewish boy hides with a family of Catholic peasant farmers to escape the Nazis.
15
Sidewalks of New York (2001)
★ 6.1/10Also comedy and drama
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…
16
Breaking & Exiting (2018)
★ 6/10Also comedy and drama
Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self…
17
Love & Sex (2000)
★ 6.2/10Also comedy and drama
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back…
18
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of…
19
(Untitled) (2009)
★ 6.3/10Also drama and comedy
A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.
20
Why Did I Get Married Again? (2026)
★ 6.7/10Also comedy and romance
The couples reunite for the destination wedding of Marcus and Angela's daughter, bringing drama old and new as they ask, "Why did we get married again?"