Movies Like My Baby Boy

If you liked My Baby Boy (2008), a movie directed by Afe Olumowe, 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
Pillow Talk (1959)
★ 7.1/10
Playboy songwriter Brad Allen's succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines. After Jan unsuccessfully lodges a…
2
Heartstopper Forever (2026)
★ 7.2/10
It's a new school year for the Truham-Higgs gang. As Nick and Charlie's relationship deepens, their thoughts turn to life after the last bell rings.
3
The Bachelor and the Bobby-Soxer (1947)
★ 6.9/10
Teenager Susan Turner, with a severe crush on playboy artist Richard Nugent, sneaks into his apartment to model for him and is found there by her sister Judge Margaret Turner. Threatened with jail, Nugent agrees to…
4
Sweet November (2001)
★ 6.9/10
Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out…
5
Marked Men: Rule + Shaw (2025)
★ 6.7/10
Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — even if she’s the only one who can see…
6
The Object of My Affection (1998)
★ 5.8/10
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
7
Prizzi's Honor (1985)
★ 6.4/10
Charley Partanna is a hitman who works for the Prizzis, one of the richest crime families in the US. When he sees Irene Walker, it's love at first sight. But he soon finds that she, too, is a killer for hire. Charley…
8
Love Me Love Me (2026)
★ 6.1/10
After her brother's death, June moves to Milan for a fresh start, finding comfort in Will, the perfect honor student at her new international school. But when his troubled best friend James—hiding a dangerous life in…
9
Magic Mike's Last Dance (2023)
★ 6.4/10
Mike Lane takes to the stage again after a lengthy hiatus, following a business deal that went bust, leaving him broke and taking bartender gigs in Florida. For what he hopes will be one last hurrah, Mike heads to…
10
Chasing Papi (2003)
★ 6.7/10
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored…
11
Love in the Afternoon (1957)
★ 7/10
A middle-aged playboy becomes fascinated by the daughter of a private detective who has been hired to entrap him with a client's wife.
12
June and John (2025)
★ 6.1/10
John leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his…
13
What's New Pussycat? (1965)
★ 5.9/10
A playboy who refuses to give up his hedonistic lifestyle to settle down and marry his true love seeks help from a demented psychoanalyst who is having romantic problems of his own.
14
Sabrina (1954)
★ 7.5/10
After two years in Paris, chauffeur's daughter Sabrina returns home elegantly transformed and immediately catches the attention of David, the playboy son of her father's rich employers. David woos and wins Sabrina, who…
15
Creed III (2023)
★ 7.1/10
After dominating the boxing world, Adonis Creed has thrived in his career and family life. When a childhood friend and former boxing prodigy, Damian Anderson, resurfaces after serving a long sentence in prison, he is…
16
The Wrong Paris (2025)
★ 6.7/10
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
17
Grown Ups (2010)
★ 6.4/10
After their high school basketball coach passes away, five good friends and former teammates reunite for a Fourth of July holiday weekend.
18
Star 80 (1983)
★ 6.5/10
Paul Snider is a narcissistic, small time hustler who fancies himself a ladies man. His life changes when he meets Dorothy Stratten working behind the counter of a Dairy Queen. Under his guidance Dorothy grows to fame…
19
Lonesome (1928)
★ 7.5/10
Two lonely people in the big city meet and enjoy the thrills of an amusement park, only to lose each other in the crowd after spending a great day together. Will they ever see each other again?
20
Down with Love (2003)
★ 6.1/10
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.