At the start of 2008, Saturday Night Live was wondering who should play presidential candidate Barack Obama (who probably wasn’t going to win the nomination, but still). If they were going to go with a Black cast member, that would have to be Kenan Thompson, who didn’t quite fit the part. They could always see if Darrell Hammond could nail Obama, and they could paint his face dark if so—everyone loved Hammond’s Jesse Jackson impression, right?

In the end, they went with Fred Armisen. Fred isn’t Black, and they would in fact darken his face for the part, but Fred’s got just enough mixed ancestry that he’s known for playing all kinds of races. A couple years later, they hired another Black cast member, Jay Pharoah, and a couple years after that, Jay took over Obama from Fred.

But they only went with Fred because their first choice didn’t work out. In 2008, halfway through the season, they offered a spot on their roster to Jordan Peele, planning for him to be their Obama. It wouldn’t be the last time they brought someone on mainly to play a politician. This past season, they grabbed James Austin Johnson, famous on the internet for his Trump impression, after years of making people suffer through Alec Baldwin. 

Peele was on MADtv when SNL offered him the part. NBC hoped Fox would let him out of his contract, which would end in a few months anyway. Well, Fox ... did not. Peele would go on to resent Fox for this for the rest of his life and would refuse to show up at the eventual MADtv reunion. Or, maybe he’s playing up his beef with Fox for laughs, but he sure has a reason to resent Fox. 

MADtv ended in 2009, just a few months into Obama’s first term, and just a little bit into what might have been a long SNL Peele tenure. Three years later, though, Peele started a new sketch show with another MADtv alum, Keegan-Michael Key. People didn’t expect much from the show at first. When has a knock-off of MAD ever been good?

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For more SNL what-ifs, check out:

8 Comedy Greats Who Have Never Hosted SNL

Three Candidates to Succeed Lorne Michaels

Rejected Saturday Night Live Sketches We'll Never Get To See

Top image: Comedy Central

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