30 most shocking moments in late night history

11. Michael Richards apologizes for racist rant on Letterman

While Michael Richards had been a beloved television star based on his run on Seinfeld, his comedy career sort of came to an end when he was involved in a racist scandal in 2006. After supposedly being heckled by African-American members of the audience during a comedy show, Richards lost his temper and dove into a horrible rant in which he said some very racist statements.

Unfortunately for Richards, the outburst was caught on camera and made available online, where millions of people watched the appalling footage. This meant damage control needed to be done if Richards wanted to salvage his career in any way, but his former co-star Jerry Seinfeld came up with an idea to help. Using time from his own appearance on The Late Show with David Letterman, Seinfeld arranged for Richards to appear on the show via satellite to give a public apology for his actions.

What followed was a very cringeworthy segment with Richards attempting to force out an apology in the midst of the studio audience laughing at him every step of the way, with Seinfeld himself pleading with them to stop. They eventually did out of respect for Jerry, but watching the entire bit is very uncomfortable.

Next: 10. Another Cramer gets roasted