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Movies Like Careless
Find movies like Careless using TMDB similarity plus Movie Rankings community context. Our top current pick is Psych: The Movie. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.
These picks blend TMDB similar-title seeds with Movie Rankings community ranking context.
Language ranking
See how Careless compares with other top-ranked English comedy movies.
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See where Careless lands among the top-ranked movies associated with Friday Night Entertainment.
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Psych: The Movie
2017
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and, of course, food!
Prom Pact
2023
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.
Shadow of the Thin Man
1941
High society sleuths Nick and Nora Charles run into a variety of shady characters while investigating a race-track murder.
Date with an Angel
1987
Aspiring composer Jim Sanders is engaged to spoiled rich girl Patty. But the morning after his bachelor party, Jim wakes up to discover a beautiful, broken-winged angel in his pool. When everyone finds out about his heavenly houseguest, Jim must cope with a dangerously jealous fiancée, an exploitive future father-in-law and a group of buddies with an outrageous business plan!
Holiday Harmony
2022
A likeable and talented underdog gets momentarily sidelined from chasing her musical dreams when her van breaks down in a welcoming small town just before Christmas.
The Thursday Murder Club
2025
A group of senior sleuths passionate about solving cold cases get plunged into a real-life murder mystery in this comic crime caper.
Flora & Ulysses
2021
When Flora rescues a squirrel she names Ulysses, she is amazed to discover he possesses unique superhero powers, which take them on an adventure of humorous complications that ultimately change Flora's life--and her outlook--forever.
The Cheap Detective
1978
A spoof of the entire 1940s detective genre. San Francisco private detective, Lou Pekinpaugh is accused of murdering his partner at the instigation of his mistress—his partner's wife.
Foul Play
1978
A shy San Francisco librarian and a bumbling cop fall in love as they solve a crime involving albinos, dwarves, and the Catholic Church.
The Late Show
1977
Over-the-hill gumshoe in Los Angeles seeks to avenge the killing of an old pal, another detective who was involved in a case concerning a murdered broad, stolen stamps, a nickel-plated handgun, a cheating dolly, and a kidnapped pussycat.
Wrong
2012
Dolph Springer wakes up one morning to realize he has lost the love of his life, his dog, Paul. During his quest to get Paul (and his life) back, Dolph radically changes the lives of others -- risking his sanity all the while.
Zero Effect
1998
Daryl Zero is a private investigator and—along with his assistant, Steve Arlo—he solves impossible crimes and puzzles. Although Daryl's a master investigator, he doesn't know what to do with himself when he's not working; he has no social skills, writes bad music and drives Steve crazy.
Wedding Season
2022
Pressured by their immigrant parents to find spouses, two Indian-Americans pretend to date in order to survive a summer of weddings – but find themselves falling for each other as they struggle to balance who they are with who their parents want them to be.
Love Potion No. 9
1992
Unlucky in love, chemist Paul Matthews visits gypsy Madame Rosa for help. Quickly realizing he is a hopeless nerd, she gifts him with Love Potion No. 8, which makes anyone who wears it irresistible to the opposite sex for four hours. Paul and animal psychologist coworker Diane Farrow decide to test it on themselves. The awkward pair suddenly find themselves alluring to anyone they approach, but soon realize they are most attracted to each other.
Heartbreakers
2001
Max and Page are a brilliant mother/daughter con team who have their grift down to a fine science. Max targets wealthy, willing men and marries them. Page then seduces them, and Max catches her husband in the act. Then it's off to palimony city and the next easy mark.
Love Birds
2011
Sometimes the best things in life happen on the fly. From the moment an injured duck crash-lands on Doug's roof, everything changes. Recently dumped and wallowing in self pity, Doug decides to nurse Pierre back to health with the assistance of an eccentric vet and bird specialist, Holly.
Who's Harry Crumb?
1989
Harry Crumb is a bumbling and inept private investigator who is hired to solve the kidnapping of a young heiress which he's not expected to solve because his employer is the mastermind behind the kidnapping.
Love, Weddings & Other Disasters
2020
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
What are the best movies like Careless?
Psych: The Movie is the strongest current recommendation on this page for viewers looking for movies like Careless.
How many recommendations are on the Careless page?
This page currently lists 18 related titles for Careless.
How often does the Movies Like Careless page update?
This page refreshes whenever Movie Rankings rebuilds the related-title view for Careless. It was last generated from site data on May 4, 2026.
Sources & freshness
Last refreshed from site data on May 4, 2026.