Movies Like Leatherheads

If you liked Leatherheads (2008), a comedy and romance movie directed by George Clooney, 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
Jerry Maguire (1996)
★ 7/10Also comedy and drama
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…
2
Varsity Blues (1999)
★ 6.2/10Also comedy and drama
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…
3
Happiness for Beginners (2023)
★ 6.2/10Also romance and comedy
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.
4
Drive Me Crazy (1999)
★ 6.6/10Also romance and comedy
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…
5
L.A. Without a Map (1999)
★ 5.8/10Also drama and comedy
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…
6
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…
7
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…
8
Dear John (2010)
★ 6.8/10Also drama and romance
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…
9
Love in Taipei (2023)
★ 6.8/10Also romance and comedy
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.
10
The High Note (2020)
★ 7/10Also romance and comedy
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…
11
Coyote Ugly (2000)
★ 6.3/10Also comedy and drama
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…
12
A California Christmas (2020)
★ 6.4/10Also comedy and romance
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.
13
Love Everlasting (2016)
★ 7.4/10Also romance and drama
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.
14
Grace (2018)
★ 6.1/10Also comedy and drama
A famous writer begins suffering from a crippling case of writer's block. His agent sends him a strange, belligerent woman to be his new assistant, hoping the change will inspire him.
15
Jersey Girl (2004)
★ 6.2/10Also comedy and romance
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…
16
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
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.
17
Purple Hearts (2022)
★ 8/10Also romance and drama
An aspiring musician agrees to a marriage of convenience with a soon-to-deploy Marine, but a tragedy soon turns their fake relationship all too real.
18
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…
19
The Life List (2025)
★ 6.9/10Also romance and comedy
When her mother sends her on a quest to complete a teenage bucket list, a young woman uncovers family secrets, finds romance — and rediscovers herself.
20
Not Easily Broken (2009)
★ 6.3/10Also drama and romance
A car accident and shifting affections test the bond between a married couple.