Movies Like Playboy's 50th Anniversary Celebration

If you liked Playboy's 50th Anniversary Celebration (2003), a movie directed by Ryan Polito, 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
Being the Ricardos (2021)
★ 6.5/10
Lucille Ball and Desi Arnaz face a crisis that could end their careers and another that could end their marriage.
2
Popstar: Never Stop Never Stopping (2016)
★ 6.6/10
When his new album fails to sell records, pop/rap superstar Conner4real goes into a major tailspin and watches his celebrity high life begin to collapse. He'll try anything to bounce back, anything except reuniting…
3
The Fresh Prince of Bel-Air Reunion (2020)
★ 8.1/10
Join Will Smith, Tatyana Ali, Karyn Parsons, Joseph Marcell, Daphne Maxwell Reid, Alfonso Ribeiro and DJ Jazzy Jeff, for a funny and heartfelt night full of music and dancing in honor of the show that ran for six…
4
Hannah Montana 20th Anniversary Special (2026)
★ 7.1/10
Filmed in front of a live studio audience and hosted by Alex Cooper of 'Call Her Daddy' fame, Miley Cyrus reflects on the creation and impact of the series with never-before-seen archival footage, all the while…
5
CBGB (2013)
★ 6.4/10
A look at New York's dynamic punk rock scene through the lens of the ground-breaking Lower East Side club started by eccentric Hilly Kristal in 1973 which launched thousands of bands.
6
Celebrity (1998)
★ 6/10
The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of…
7
X-Rated 2: The Greatest Adult Stars of All Time (2016)
★ 6.8/10
Documentary sequel that offers a close-up look into the personal lives of the legendary porn stars who've survived the test of time and influenced popular culture. Blends rare interviews with erotic clips and…
8
Michael Bolton's Big, Sexy Valentine's Day Special (2017)
★ 6/10
After Santa tells Michael Bolton that he needs 75,000 new babies by Christmas to meet toy supply, he hosts a sexy telethon to get the world to start making love.
9
Sly (2023)
★ 7.2/10
His love of film began as an escape from a rocky childhood. From underdog to Hollywood legend, Sylvester Stallone tells his story in this documentary.
10
Life (2015)
★ 6/10
In 1955, young photographer Dennis Stock develops a close bond with actor James Dean while shooting pictures of the rising Hollywood star.
11
Down with Love (2003)
★ 6.1/10
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.
12
Bachelor Party (1984)
★ 6.3/10
On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.
13
Insignificance (1985)
★ 6.4/10
Four 1950s icons meet in the same hotel room, and two of them discover more in common between them than they ever anticipated.
14
Pecker (1998)
★ 6.1/10
A Baltimore teenager who picks up a second-hand camera starts snapping his way to stardom, soon turning into a nationwide sensation, with a fateful choice between his life and his art.
15
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…
16
Shine a Light (2008)
★ 6.8/10
Martin Scorsese’s electrifying concert documentary captures The Rolling Stones live at New York’s Beacon Theatre during their A Bigger Bang tour. Filmed over two nights in 2006 with an all-star team of…
17
Elvis (2022)
★ 7.4/10
The life story of Elvis Presley as seen through the complicated relationship with his enigmatic manager, Colonel Tom Parker.
18
The Philadelphia Story (1940)
★ 7.5/10
When a rich woman's ex-husband and a tabloid-type reporter turn up just before her planned remarriage, she begins to learn the truth about herself.
19
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…
20
Blue Moon (2025)
★ 6.7/10
On the evening of March 31, 1943, legendary lyricist Lorenz Hart confronts his shattered self-confidence in Sardi’s bar as his former collaborator, Richard Rodgers, celebrates the opening night of his ground-breaking…