Phil Hartman became a star during his time on Saturday Night Live, with a wide range of comedic characters, but the end of his life – 20 years ago today – was nothing short of a tragedy.

I had just finished my freshman year of college not long before the day Phil Hartman was murdered by his wife on May 28, 1998, and I remember hearing the news report that he had died. After an argument about her substance abuse in the day’s early hours, Hartman went to bed, but he never woke up. His wife of 11 years, Brynn, took a gun and shot him three times before later killing herself.

The tragic domestic dispute took one of the funniest people to ever appear on television. After some bit parts in movies and cartoon voice work, Hartman became a cast member on SNL in 1986. Over the course of 8 seasons on the variety show, Hartman portrayed dozens of characters. My favorite original Hartman character was, I think, Unfrozen Caveman Lawyer, which debuted in 1991. In the sketch, Hartman portrayed Keyrock, a Neanderthal frozen in the ice for 100,000 years who was thawed out and went to law school.

It was his impressions, though, that really put Hartman over the top in terms of his popularity on Saturday Night Live. The comedian did unforgettable versions of Ed McMahon, Frank Sinatra, Donald Trump and Charlton Heston. But none of those compare to how he defined the first half of Bill Clinton’s presidency.

Hartman was also an integral part of THE SIMPSONS, starting with the show’s second season. Hartman provided the voices of Hollywood has-been Troy McClure and ambulance chaser Lionel Hutz. Of all of the secondary characters that have been a part of the animated show over the years, Hartman’s characters were some of the most memorable of the show’s first decade. Matt Groening and the rest of the show’s team had so much respect for Hartman’s contributions, they retired the characters after he died.

But my favorite Phil Hartman role was in the NBC sitcom NEWSRADIO. Hartman played radio news anchor Bill McNeil in the show, which focused on a midwestern radio producer taking over as news director for a New York City news radio station. Hartman was part of an ensemble that included Dave Foley, Maura Tierney, Stephen Root, Andy Dick and Joe Rogan, and he managed to stand out in every episode, even if he only had a small part. Newsradio is one of my favorite comedies of the 1990s, and Hartman plays a large part of that. After his death, the show continued for a fifth season with Jon Lovitz taking Hartman’s place, but it wasn’t the same.

What are your favorite Phil Hartman moments? Talk about it in the comments.