Movies Like Playboy's Private Diaries

If you liked Playboy's Private Diaries (1994), a movie directed by Steve Conte, 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 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…
2
It Happened One Night (1934)
★ 7.8/10
A runaway heiress makes a deal with the rogue reporter trailing her but the mismatched pair end up stuck with each other when their bus leaves them behind.
3
Big Trouble (2002)
★ 6.1/10
The story of how a mysterious suitcase brings together, and changes, the lives of a divorced dad, an unhappy housewife, two hitmen, a pair of street thugs, two love struck teens, two FBI men and a psychedelic toad…
4
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
5
Black Beauty (2020)
★ 8/10
Born free in the American West, Black Beauty is a horse rounded up and brought to Birtwick Stables, where she meets spirited teenager Jo Green. The two forge a bond that carries Beauty through the different chapters…
6
Propeller One-Way Night Coach (2026)
★ 6.2/10
During the golden age of aviation, a young airplane enthusiast and his mother embark on a cross-country journey to Hollywood—and their simple flight transforms into the trip of a lifetime.
7
Don't Bother to Knock (1952)
★ 6.6/10
An airline pilot pursues a live-in babysitter at his hotel and gradually realizes she is not as stable as perhaps she should be.
8
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.
9
Libeled Lady (1936)
★ 7.3/10
When a major newspaper accuses wealthy socialite Connie Allenbury of being a home-wrecker, and she files a multi-million-dollar libel lawsuit, the publication's frazzled head editor, Warren Haggerty, must find a way to…
10
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…
11
Father Hood (1993)
★ 5.8/10
Deadbeat dad kidnaps his kids from the bus to an abusive foster home and they go on a run. The cops are after them, they bicker constantly and his idea of a way out is grim, yet this dangerous ride might just turn them…
12
That Hamilton Woman (1941)
★ 7.1/10
The story of courtesan and dance-hall girl Emma Hamilton, including her relationships with Sir William Hamilton and Admiral Horatio Nelson and her rise and fall, set during the Napoleonic Wars.
13
Reflections in a Golden Eye (1967)
★ 6.5/10
Bizarre tale of sex, betrayal, and perversion at a military post.
14
Ploey: You Never Fly Alone (2018)
★ 6.2/10
A plover chick has not learned to fly when his family migrates in the fall. He must survive the arctic winter, vicious enemies and himself in order to be reunited with his beloved one next spring.
15
A Matter of Life and Death (1946)
★ 7.7/10
A British wartime aviator who cheats death must argue for his life before a celestial court, hoping to prolong his fledgling romance with an American girl.
16
Tinker Bell and the Great Fairy Rescue (2010)
★ 6.8/10
During a summer stay on the mainland, Tinker Bell is accidentally discovered while investigating a little girl's fairy house. As the other fairies, led by the brash Vidia, launch a daring rescue in the middle of a…
17
Return to Never Land (2002)
★ 6.5/10
In 1940, the world is besieged by World War II. Wendy, all grown up, has two children; including Jane, who does not believe Wendy's stories about Peter Pan.
18
Lady and the Tramp II: Scamp's Adventure (2001)
★ 6.3/10
Lady and Tramp's mischievous pup, Scamp, gets fed up with rules and restrictions imposed on him by life in a family, and longs for a wild and free lifestyle. He runs away from home and into the streets where he joins a…
19
The Sleeping Dictionary (2003)
★ 6.6/10
In the 1930s, British officer John Truscott journeys to a remote village in colonial Malaysia to educate and Westernize the local Iban population. There, he's introduced to the lovely Selima. In keeping with tradition…
20
Mata Hari (1931)
★ 6.2/10
A semi-fictionalized account of the life of Mata Hari, an exotic dancer who was accused of spying for Germany during World War I.