Most Similar Movies to Man of the Century (1999)
If you are looking for movies like Man of the Century (1999), you might like movies tagged with keyword : comedy, black and white, nostalgia, retro, humorous, independent film, new york, journalist, 1920s, jazz, romantic, witty, dialogue-driven, character-driven, low budget, quirky, stylized, fast-paced, love, urban .
Damsels in Distress (2011), San Diego, I Love You (1944), Spring Fever (1927), Carry on Spying (1964), Eternity: The Movie (2014), Swingers (1996), Safety Not Guaranteed (2012) ... Let's take a look at the following list...

Damsels in Distress (2011)
A trio of girls set out to change the male-dominated environment of the Seven Oaks college campus, and to rescue their fellow students from depression, grunge and low standards of every kind.
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San Diego, I Love You (1944)
A harried daughter tries to keep her wacky family together while trying to sell her eccentric father's latest invention, a collapsible life raft.
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Spring Fever (1927)
To impress a wealthy young woman, a clerk pretends he is a pro-golfer.
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Carry on Spying (1964)
A British spy (Kenneth Williams) and his pupils are sent to recover a secret formula stolen by an agent of STENCH.
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Eternity: The Movie (2014)
Todd Lucas is a naive songwriter from the Midwest. BJ Fairchild is a brash saxophonist from The Valley. Alone, they are pathetic losers. Together, they form the most mediocre R&B duo of the 1980s - Eternity.
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Swingers (1996)
Wannabe actors become regulars in the stylish neo-lounge scene; Trent teaches his friend Mike the unwritten rules of the scene.
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Safety Not Guaranteed (2012)
Three magazine employees head out on an assignment to interview a guy who placed a classified advertisement seeking a companion for time travel.
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Zero Effect (1998)
The world's greatest detective Daryl Zero aided by his associate Steve Arlo investigates a complex and mysterious case of blackmail and missing keys for shady tycoon Gregory Stark who is less than forthcoming about what is really happening!
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The Pleasure of His Company (1961)
San Francisco debutante, Jessica Poole, is marrying Napa Valley cattle rancher, Roger Henderson, and hopes her peripatetic father, "Pogo" Poole, whom she hasn't seen for years, comes to the wedding. He arrives, disrupting the household of his ex-wife, Katharine, and her long-suffering husband, and befriending their cook, Toy. At first it seems that Pogo is set on brea...Read all
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Liberal Arts (2012)
When 30-something Jesse returns to his alma mater for a professor's retirement party, he falls for Zibby, a college student, and is faced with a powerful attraction that springs up between them.
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Topper Takes a Trip (1939)
To gain entry to Heaven, a ghost attempts to reunite a divorcing couple as a good deed.
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Gumshoe (1972)
Inspired by his love for Dashiell Hammett novels, nightclub comedian Eddie Ginley puts an ad in the paper as a private eye. The case he gets turns out to be a strange setup and as he digs to the bottom of it his life starts falling apart.
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Here Comes the Groom (1951)
Foreign correspondent Pete Garvey has 5 days to win back his former fiancée, or he'll lose the orphans he adopted.
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Greenwich Village (1944)
In 1922, a would-be classical composer gets involved with people putting on a musical revue.
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Step Lively (1944)
Gordon Miller is rehearsing a musical comedy in the penthouse suite of Gribble's hotel...on credit. The mounting bill is driving Gribble frantic. Chaos increases when playwright Glen Russell, whose dramatic play he thinks Miller is producing, arrives. But it turns out Russell can sing like Sinatra, and Miller has leading lady Christine turn on the charm. Can Miller's ...Read all
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Down Memory Lane (1949)
This film is a compilation, with narration by Steve Allen, of comedies from the old Mack Sennett silent studio. Sennett, himself, appears in a cameo at the end of the film.
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A New Kind of Love (1963)
The fashion industry and Paris provide the setting for a comedy surrounding the mistaken impression that Samantha Blake is a high-priced call girl. Steve Sherman is the journalist interviewing her for insights on her profession.
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Going Places (1939)
A sports store clerk poses as a famous jockey as an advertising stunt, but gets more than he bargained for.
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