The Fresh Prince of Bel-Air’s Greatest Guest Stars

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A little known fact: We, the world, owe the existence of The Fresh Prince of Bel-Air to Will Smith’s financial difficulties. In the heady late 1980s, Smith had squandered his earnings from his rap career and was in deep trouble with the IRS when he was approached by a WB executive about starring in a new show, loosely based on his own persona. Smith’s compromise was our sitcom gain: who can deny the hilarity of the smooth-talking Prince’s dancing or his constant goof-ups with partner-in-crime Jazzy Jeff? Over the six years of the show, Fresh Prince was not only fun, it was culturally relevant. A Young Kathy Griffin had her first television break on the show; and the program hosted numerous big name guests, from Oprah Winfrey to Chris Rock. After the jump, our roundup of some of the best guest stars on The Fresh Prince of Bel-Air.

Tyra Banks

The best part of this clip is seeing the now perpetually-svelte Banks in haute ’90s casual — cut-off shirt, flood pants, and a messy ponytail. Tres chic!

Bill Biv Devoe

Whenever Will threw a party, awesome things seemed to happen. Like smoke machines! Or the sudden, unexplained appearance of short-lived sensation and New Edition spin-off Bill Biv Devoe.

Boyz II Men

No Christmas would be complete without some sort of heart-warming harmonious musical number. And who better to deliver that — in a very special episode — than those kings of heart manipulation, Boyz II Men.

Don Cornelius/Soul Train

In this quasi-crossover episode, the Banks gang with Will in tow get to dance on Soul Train. Hilarity and break-dancing ensue.

Evander Holyfield

Will Smith and Jazzy Jeff released a single called “I Think I Can Beat Mike Tyson,” so it only seems appropriate that the Prince would have on Holyfield, who actually beat Mike Tyson. Twice.

Tom Jones

After Carlton’s amazing Tom Jones impression, it was only a matter of time before the man himself made an appearance on the show. And boy, what an appearance. That Carlton-Jones duet is one for the history books.

Chris Rock

Rock appears at about the five-minute mark of this clip, and he’s delightful. Though you sort of want to muffle Uncle Banks’ ears before he turns blue.

William Shatner

On this episode, William Shatner, playing himself, goes on Vivian’s show and gets a tooth broken by Smith. The interactions between Shatner and Smith are priceless.

Oprah Winfrey

Smith and family go on one of Oprah’s shows in this episode, and are accordingly granted a guest appearance by the queen of media herself.

Milo Ventimiglia

Before he was a Heroes heart-throb, Ventimiglia was a doofy party guest of Vivian’s.