Movies like Leatherheads (2008)
The best movies like Leatherheads (2008) are Jerry Maguire (1996), Varsity Blues (1999) and Drive Me Crazy (1999). If Leatherheads hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedVanishing Point (1971)7.1/10 from 559 votes
- NewestThe Baltimorons (2025)Released 2025
Jerry Maguire (1996)
Jerry Maguire used to be a typical sports agent: willing to do just about anything he could to get the biggest possible contracts for his clients, plus a nice commission for himself. Then, one day, he suddenly has second thoughts about what he's really doing. When he voices these doubts, he ends up losing his job and all of his clients, save Rod Tidwell, an egomaniacal football player.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisVarsity Blues (1999)
In small-town Texas, high school football is a religion, 17-year-old schoolboys carry the hopes of an entire community onto the gridiron every Friday night. When star quarterback Lance Harbor suffers an injury, the Coyotes are forced to regroup under the questionable leadership of John Moxon, a second-string quarterback with a slightly irreverent approach to the game.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisDrive Me Crazy (1999)
Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisHappiness for Beginners (2023)
At a crossroads after her divorce, a schoolteacher ventures toward a fresh start in life — and love — when she signs up for a grueling group hiking trip.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisA California Christmas (2020)
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisHe Said, She Said (1991)
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 alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisL.A. Without a Map (1999)
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
Why it matches: Recommended by TMDB viewers · both drama & comedy
SnoozefestMovies like thisWhich Brings Me to You (2023)
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 messy histories and heartbreak, on the off chance that this fling might be the real thing.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisFather of the Bride (1950)
Proud father Stanley Banks remembers the day his daughter, Kay, got married. Starting when she announces her engagement through to the wedding itself, we learn of all the surprises and disasters along the way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisLove in Taipei (2023)
A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisCoyote Ugly (2000)
Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and notoriety she receives at her "day" job as a barmaid at Coyote Ugly. The "Coyotes" as they are affectionately called tantalize customers and the media alike with their outrageous antics, making Coyote Ugly the watering hole for guys on the prowl.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe High Note (2020)
Set in the dazzling world of the LA music scene comes the story of Grace Davis, a superstar whose talent, and ego, have reached unbelievable heights. Maggie is Grace’s overworked personal assistant who’s stuck running errands, but still aspires to her childhood dream of becoming a music producer. When Grace’s manager presents her with a choice that could alter the course of her career, Maggie and Grace come up with a plan that could change their lives forever.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisChéri (2009)
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisJersey Girl (2004)
Ollie Trinke is a young, suave music publicist who seems to have it all, with a new wife and a baby on the way. But life deals him a bum hand when he's suddenly faced with single fatherhood, a defunct career and having to move in with his father. To bounce back, it takes a new love and the courage instilled in him by his daughter.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSon in Law (1993)
Country girl Rebecca has spent most of her life on a farm in South Dakota, and, when she goes away to college in Los Angeles, Rebecca immediately feels out of place in the daunting urban setting. She is befriended by a savvy party animal named Crawl, who convinces the ambivalent Rebecca to stay in the city. When Thanksgiving break rolls around, Rebecca, no longer an innocent farm girl, invites Crawl back to South Dakota, where he pretends to be her fiancé.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Baltimorons (2025)
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove on the Sidelines (2016)
A down-on-her-luck young woman who falls into a job as a personal assistant to a star quarterback sidelined with an injury. He's never had a female assistant before and she knows nothing about football.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisDear John (2010)
While Sergeant John Tyree is home on two weeks leave from Germany, he meets Savannah after he dives into the ocean to retrieve Savannah's purse that had fallen off a pier. John eventually falls in love with Savannah, who promises to write to him until he returns from overseas.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisLove Everlasting (2016)
Bridger is a young outsider who's always wanted more. He and his mother flee an abusive home, eventually finding a small town in the middle of nowhere. Once there, Bridger finds true acceptance with another misfit.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisLucas (1986)
A brilliant but socially inept 14-year-old experiences heartbreak for the first time when his two best friends – Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love – fall for each other.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisShort Circuit 2 (1988)
Robot Johnny 5 moves to the city to help his friend Ben Jahrvi with his toy manufacturing enterprise, only to be manipulated by criminals who want to use him for their own nefarious purposes.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisSea of Love (1989)
Seen-it-all New York detective Frank Keller is unsettled - he has done twenty years on the force and could retire, and he hasn't come to terms with his wife leaving him for a colleague. Joining up with an officer from another part of town to investigate a series of murders linked by the lonely hearts columns he finds he is getting seriously and possibly dangerously involved with Helen, one of the main suspects.
Why it matches: Similar story and style · both drama & romance
Popcorn FlickMovies like thisHeaven Can Wait (1978)
Joe Pendleton is a quarterback preparing to lead his team to the superbowl when he is almost killed in an accident. An overanxious angel plucks him to heaven only to discover that he wasn't ready to die, and that his body has been cremated. A new body must be found, and that of a recently-murdered millionaire is chosen. His wife and accountant—the murderers—are confused by this development, as he buys the L.A. Rams in order to once again quarterback them into the Superbowl.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisThe Paper (1994)
Henry Hackett, a workaholic tabloid editor, has to juggle personal issues, difficult coworkers, a tempting job offer, a looming deadline and a race to land an exclusive on a recent high-profile murder case, all during one hectic workday.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisBreakfast of Champions (1999)
A millionaire car salesman who runs the biggest dealership in Midland City, Dwayne Hoover is a celebrity, loved and trusted by everyone. Then one day, he wakes up and realizes that his life is a total mess! But between the headaches posed by his pill-popping wife, a mistress who won't leave him alone, and a cross-dressing sales manager, Dwayne has picked a bad week for a midlife crisis.
Why it matches: Similar story and style · both comedy & drama
SnoozefestMovies like thisGridlock'd (1997)
After a friend overdoses, Spoon and Stretch decide to kick their drug habits and attempt to enroll in a government detox program. Their efforts are hampered by seemingly endless red tape, as they are shuffled from one office to another while being chased by drug dealers and the police.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisRock Star (2001)
A wannabe rock star who fronts a Pennsylvania-based tribute band is devastated when his bandmates kick him out of the group he founded. Things begin to look up for Izzy when he is asked to join Steel Dragon, the heavy metal rockers he had been imitating for so long. This film is loosely based on the true story of the band Judas Priest.
Why it matches: Similar story and style · both drama & comedy
Popcorn FlickMovies like thisSavage Fire (2017)
In the city of Cajamar, in the middle of ruined nature, lonely characters deal with the police, rodeos and mysterious fires.
Why it matches: Similar story and style · both drama
Vanishing Point (1971)
Kowalski works for a car delivery service, and takes delivery of a 1970 Dodge Challenger to drive from Colorado to San Francisco. Shortly after pickup, he takes a bet to get the car there in less than 15 hours.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Leatherheads?
The closest matches to Leatherheads are Jerry Maguire (1996), Varsity Blues (1999) and Drive Me Crazy (1999). Below are 27 more, each with the reason it matches.
What should I watch after Leatherheads?
Start with Jerry Maguire (1996), the closest match to Leatherheads.
What is the highest-rated movie like Leatherheads?
Vanishing Point (1971), rated 7.1/10 by 559 TMDB users.
What is the newest movie like Leatherheads?
The Baltimorons (2025) is the most recent release on this list.
Are there English movies like Leatherheads?
Yes: Jerry Maguire (1996), Varsity Blues (1999) and Drive Me Crazy (1999).
How are movies similar to Leatherheads chosen?
First come films that Trakt’s viewers watch alongside Leatherheads, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.