49. He Nearly Suffocated Richard Simmons
Maybe one of Letterman's most infamous feuds was with fitness guru Richard Simmons. Simmons appeared on Late Night and Late Show all the time, and the pair seemed to have a pretty close relationship—but that all crashed and burned after an appearance in 2000. Simmons was dressed as a turkey (just roll with it) and Letterman sprayed him in the face with a fire extinguisher (just roll with it).
Unfortunately, the results were disastrous.
Simmons suffers from severe asthma, and the blast from the fire extinguisher resulted in a brutal asthma attack. Letterman made light of the incident, and Simmons was furious. He didn't come back on the show for over six years afterward.










