#12: The Time He Roasted Gilda Radner—Right After Her Death
In 1989, shortly after the beloved SNL comedian Gilda Radner passed away from cancer, Howard Stern aired a segment where he mocked her death on his show, even making jokes about her appearance during her illness.

Fans and fellow comedians were furious. Many considered it one of Stern’s most tasteless moments, crossing a line between dark humor and outright cruelty. While Stern often defended his style as “equal opportunity offense,” this particular bit left a lasting scar—and reminded audiences that no one, not even comedy legends, were off-limits in his world.
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