Most Popular Wealthy Playboy Movies and TV Shows
2. Under Eighteen (1931)
80 min | Drama, Romance
A poor seamstress girl sours on her engagement to a grocery deliveryman after seeing her sister's abusive marriage. Trying to help her sister pay for a divorce lawyer, she turns to a rich playboy she met at work.
3. She Knew All the Answers (1941)
Approved | 85 min | Comedy
A chorus girl, Gloria Winters, is overjoyed that wealthy young Randy Bradford is so eager to marry her, he's asked her to elope. Before they can leave, Randy is contacted by Mark Willows, ... See full summary »
4. The Isle of Hope (1925)
Passed | Action, Adventure, Drama
A ship captain's beautiful daughter and a wealthy playboy who is searching for buried treasure find themselves stranded on a desert island.
6. Two Weeks with Pay (1921)
Passed | Comedy, Romance
Pansy O'Donnell, a salesgirl, is given a two-week vacation at a summer resort, where she advertises clothing made by her company. The hotel clerk mistakes her for movie actress Marie La ... See full summary »