Movies Like Lena's Holiday

If you liked Lena's Holiday (1991), a comedy and drama movie directed by Michael Keusch, 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
Pink Floyd: The Wall (1982)
★ 8/10Also drama
A troubled rock star descends into madness in the midst of his physical and social isolation from everyone.
2
Landline (2017)
★ 6.2/10Also comedy and drama
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
3
Psycho Therapy: The Shallow Tale of a Writer Who Decided to Write About a Serial Killer (2025)
★ 6.8/10Also comedy
A struggling writer in the midst of a divorce befriends a retired serial killer who incidentally becomes his marriage counselor by day, and killing counselor for his next book by night.
4
The Naked City (1948)
★ 7.2/10Also drama
After a former model is drowned in her bathtub, Detective James Halloran and Lieutenant Dan Muldoon attempt to piece together her murder.
5
EuroTrip (2004)
★ 6.6/10Also comedy
When Scott learns that his longtime cyber-buddy from Berlin is a gorgeous young woman, he and his friends embark on a trip across Europe.
6
Celebrity (1998)
★ 6/10Also drama and comedy
The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of…
7
The Enforcer (2022)
★ 7/10Also drama
A noir thriller set in Miami, the film follows an enforcer who discovers his femme fatale boss has branched out into cyber sex trafficking, putting a young runaway he’s befriended at risk. He sacrifices everything to…
8
The Squid and the Whale (2005)
★ 7/10Also comedy and drama
Based on the true childhood experiences of Noah Baumbach and his brother, The Squid and the Whale tells the touching story of two young boys dealing with their parents' divorce in Brooklyn in the 1980s.
9
The Good Neighbor (2022)
★ 6.7/10Also drama
A nightmarish evening unfolds for neighbors David and Robert when they accidentally hit a woman on her bike and flee the scene. While David is increasingly plagued by feelings of guilt, Robert shows no remorse and…
10
House of D (2004)
★ 6.3/10Also comedy and drama
In the present, artist Tom Warshaw recalls his traumatic coming of age. As a 13-year-old growing up in New York City in 1973, Tom hangs out with Pappass, a mentally disabled man. With Tom's mother battling depression…
11
All About Nina (2018)
★ 5.8/10Also comedy and drama
Nina Geld's passion and talent have made her a rising star in the comedy scene, but she's an emotional mess offstage. When a new professional opportunity coincides with a romantic one, she is forced to confront her own…
12
Effie Gray (2014)
★ 6/10Also drama
A look at the mysterious relationship between Victorian art critic John Ruskin and his teenage bride Effie Gray.
13
Shane Gillis: Beautiful Dogs (2023)
★ 7/10Also comedy
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
14
Match (2014)
★ 5.8/10Also comedy and drama
A Seattle couple travel to New York to interview colorful former dancer Tobi for research on a dissertation about dance. But soon, common niceties and social graces erode when the questions turn personal and the true…
15
The Spy Who Dumped Me (2018)
★ 6.4/10Also comedy
A couple of thirtysomething best friends unwittingly become entangled in an international conspiracy when one’s ex-boyfriend shows up at their apartment with a team of deadly assassins on his trail.
16
Horns (2013)
★ 6.3/10Also drama
In the aftermath of his girlfriend's mysterious death, a young man awakens to strange horns sprouting from his temples.
17
The Joneses (2010)
★ 6.2/10Also comedy and drama
A seemingly perfect family moves into a suburban neighborhood, but when it comes to the truth as to why they're living there, they don't exactly come clean with their neighbors.
18
Barton Fink (1991)
★ 7.5/10Also comedy and drama
A renowned New York playwright is enticed to California to write for the movies and discovers the hellish truth of Hollywood.
19
Adoration (2013)
★ 6.1/10Also drama
Lil and Roz are two lifelong friends, having grown up together as neighbors in an idyllic beach town. As adults, their sons have developed a friendship as strong as that which binds their mothers. One summer, all four…
20
Savage House (2026)
★ 7/10Also comedy and drama
Against the backdrop of 18th century England, a massive pox outbreak, and Jacobite uprising – Sir Chauncey Savage and Lady Savage blindly pursue a better life. It's not without a tinge of irony that their family name…