Returning to host for the second time, the Donald memorably dad-danced in this parody of Drake's "Hotline Bling" video.
Check out the Skazzy cover boy. Anyone remember this now eerily prescient mock-up magazine cover from the Brooke Shields sitcom?
He also sits in on a poker game with Judd Nelson's Jack and John McEnroe, both fellow divorcés.
Trump and his WWE CEO frenemy Vince McMahon picked surrogates to battle it out for them, Hair vs. Hair, in 2007. Trump's guy won, resulting in McMahon having his head shaved on TV.
Presumably wrestling appeals to Trump's take-no-prisoners mentality.
Who better to point a lost kid toward the lobby of The Plaza than its owner. (Trump sold the storied NYC hotel in 1995.)
The famed New Yorker says he always supported the idea of Whoopi Goldberg's contest winner coaching the Knicks all along.
Anybody who's anybody knows what a force in the male modeling world Derek Zoolander is.
Surprise! Waldo's dad is Donald Trump. Which is probably why he gets all of the coolest toys.
The real estate tycoon is ready to talk business with the big shot Whoopi Goldberg creates because she feels she has a better shot of success if she creates a male business persona.
Twist! It's Fran who knows The Donald, not her rich employer.
Of course Trump needed to meet with the mayor of NYC at some point over the sitcom's run.
Just a couple of rich New Yorkers needling each other at a cocktail party before Hugh Grant is swept off his feet by Sandra Bullock.
"What are you, morons?" he asks Kate & Co. when she fan-girls over him in the middle of the street.
Bet you forgot that the, um, older gentleman Samantha briefly dated was lunching with Donald Trump (i.e. proof he's rich) when they first met!
He pops up just long enough in the short-lived 2001-02 sitcom to ask Denis Leary's addled detective if he's "banging" Elizabeth Hurley. Not weird at all!
When the Banks family puts their house up for sale, Carlton literally swoons when Trump and then-wife Marla Maples show up to break it to them that they're buying the house next door.
NEXT GALLERY: The Kardashians' TV and movie cameos