Movies Like Tripping Through the Holidays

If you liked Tripping Through the Holidays (2025), a comedy movie directed by Harris Smith Evans, 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
The Pink Panther Strikes Again (1976)
★ 6.9/10Also comedy
Charles Dreyfus, who has finally cracked over inspector Clouseau's antics, escapes from a mental institution and launches an elaborate plan to get rid of Clouseau once and for all.
2
The Best Man Holiday (2013)
★ 6.5/10Also comedy
When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.
3
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
4
Fun with Dick and Jane (1977)
★ 6.6/10Also comedy
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
5
A Loud House Christmas (2021)
★ 7.1/10Also comedy
Lincoln Loud gears up for the ultimate Christmas, until he finds out that most of his sisters have plans to be elsewhere for the big day. Determined to remind his family that they all need to be together, Lincoln and…
6
Psych 2: Lassie Come Home (2020)
★ 7/10Also comedy
After Santa Barbara Police Chief Carlton Lassiter is ambushed and left for dead, Shawn and Gus return to help him and find themselves embroiled in a case involving the personal, the professional – and even the…
7
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
8
Me Time (2022)
★ 5.8/10Also comedy
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
9
Once Upon a Deadpool (2018)
★ 7.1/10Also comedy
A kidnapped Fred Savage is forced to endure Deadpool's PG-13 rendition of Deadpool 2, as a Princess Bride-esque story full of magic, wonder, and zero Fs.
10
Daddy's Home 2 (2017)
★ 6.3/10Also comedy
Father and stepfather Dusty and Brad join forces to make Christmastime perfect for the children. Their newfound partnership soon gets put to the test when Dusty's old-school, macho dad and Brad's gentle father arrive…
11
Hard to Die (1990)
★ 6/10Also comedy
While doing the inventory for a lingerie outlet in a high rise office building, five attractive women are terrorized by a series of bizarre killings. They suspect that the strange janitor, who witnessed another series…
12
Sextuplets (2019)
★ 6.2/10Also comedy
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
13
The Thursday Murder Club (2025)
★ 6.6/10Also comedy
A group of senior sleuths passionate about solving cold cases get plunged into a real-life murder mystery in this comic crime caper.
14
Louis C.K.: Ridiculous (2026)
★ 6.1/10Also comedy
From a bee getting shot in New York City to paying strangers to take his aging father, Louis C.K. unleashes the ridiculous thoughts in his mind.
15
Ride Along 2 (2016)
★ 6.3/10Also comedy
As his wedding day approaches, Ben heads to Miami with his soon-to-be brother-in-law James to bring down a drug dealer who's supplying the dealers of Atlanta with product.
16
Return (2015)
★ 6.6/10Also comedy
A young man returns home for the weekend to discover the difficulty of juggling friends, parents, magic mushrooms and several thousand chickens.
17
A Christmas Story Christmas (2022)
★ 6.3/10Also comedy
Follows Ralphie, now adult, who returns to the house on Cleveland Street to give his kids a magical Christmas like the one he had as a child, reconnecting with childhood friends, and reconciling the passing of his Old…
18
The Unbearable Weight of Massive Talent (2022)
★ 6.8/10Also comedy
Creatively unfulfilled and facing financial ruin, Nick Cage must accept a $1 million offer to attend the birthday of a dangerous superfan. Things take a wildly unexpected turn when Cage is recruited by a CIA operative…
19
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.
20
Driver's Ed (2026)
★ 6.9/10Also comedy
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.