From Parties at the Playboy Mansion to a Soft-Core Porn Film: Donald Trump's Long and Colorful History with Playboy
![Dec. 4, 2003 - New York, New York, U.S. - K34439RM.50TH ANNIVERSARY OF PLAYBOY AT THE ARMORY ON LEXINGTON AVENUE, NEW YORK New York .12/04/2003. / 2003.DONALD TRUMP AND MELANIA KNAUSS(Credit Image: Dec. 4, 2003 - New York, New York, U.S. - K34439RM.50TH ANNIVERSARY OF PLAYBOY AT THE ARMORY ON LEXINGTON AVENUE, NEW YORK New York .12/04/2003. / 2003.DONALD TRUMP AND MELANIA KNAUSS(Credit Image:](https://c8.alamy.com/comp/CD6HND/dec-4-2003-new-york-new-york-us-k34439rm50th-anniversary-of-playboy-CD6HND.jpg)
Dec. 4, 2003 - New York, New York, U.S. - K34439RM.50TH ANNIVERSARY OF PLAYBOY AT THE ARMORY ON LEXINGTON AVENUE, NEW YORK New York .12/04/2003. / 2003.DONALD TRUMP AND MELANIA KNAUSS(Credit Image:
![Donald Trump (center left) and Melania Knauss (center right) with Playboy Playmates at the Boss Hugo Boss Playboy & the Playboy Playmates party in celebration of the Hugo Boss New York Flagship Donald Trump (center left) and Melania Knauss (center right) with Playboy Playmates at the Boss Hugo Boss Playboy & the Playboy Playmates party in celebration of the Hugo Boss New York Flagship](https://c8.alamy.com/comp/KB830W/donald-trump-center-left-and-melania-knauss-center-right-with-playboy-KB830W.jpg)
Donald Trump (center left) and Melania Knauss (center right) with Playboy Playmates at the Boss Hugo Boss Playboy & the Playboy Playmates party in celebration of the Hugo Boss New York Flagship
![He would be a great leader,' Melania Trump said of then-boyfriend Donald Trump in 1999 ABC News interview - ABC News He would be a great leader,' Melania Trump said of then-boyfriend Donald Trump in 1999 ABC News interview - ABC News](https://s.abcnews.com/images/US/melania-knauss-trump-interview-04-abc-jc-181012_hpEmbed_21x16_608.jpg)
He would be a great leader,' Melania Trump said of then-boyfriend Donald Trump in 1999 ABC News interview - ABC News
![He would be a great leader,' Melania Trump said of then-boyfriend Donald Trump in 1999 ABC News interview - ABC News He would be a great leader,' Melania Trump said of then-boyfriend Donald Trump in 1999 ABC News interview - ABC News](https://s.abcnews.com/images/US/melania-knauss-trump-interview-01-abc-jc-181012_hpMain_16x9_992.jpg)