Phil Hartman was known for making audiences laugh on Saturday Night Live, but his death 20 years ago, on May 28, 1998, was truly shocking, an incident that rattled Hollywood and devastated his fans.

Police determined that Hartman, 49, had been shot by his wife of 10 years, 41-year-old Brynn, as he slept in their $1.4 million Encino, Calif., home. Hours later, Brynn turned the gun on herself. They left behind two children — a son, Sean, 9, and a daughter, Birgen, 6 — as well as many unanswered questions.

Hartman had left SNL after eight seasons in 1994 and was starring in his own show, cult-favorite NewsRadio. He also voiced the popular characters Lionel Hutz and Troy McClure on The Simpsons.

View photos Phil Hartman, top left, poses with his Saturday Night Live co-stars on Oct. 4, 1993. (Photo: NBC/NBCU Photo Bank) More

Brynn, a former model, was Hartman’s third wife. She had struggled with addiction to alcohol and cocaine, having checked into rehab several times in the last few months of her life. Close friends told People magazine that she had begun to drink again days before the tragedy. Jeannie Petersen, identified as a lifelong friend of Brynn, said she had wanted a divorce for two years. Others say it was Hartman who wanted out, according to People.

On the night of May 27, Brynn visited a local Buca di Beppo with a producer friend, Christine Zander. She reportedly drank two cosmopolitans over two hours. “She seemed content,” Zander said. “We made plans to see each other the following weekend.” The bartender said Brynn promised to bring Phil to the restaurant with her next time.

Watch: Hartman as Bill Clinton on SNL:

But she and Phil argued when she arrived home.

“He had made it very clear that if she started using drugs again, that would end the relationship,” said his friend Steven Small.

Brynn shot her husband around 3 a.m. as he slept, once on his right side and twice in the head, with a .38-caliber handgun that he kept in a safe. She then went to a friend’s house in a panic and confessed. Brynn returned home with the friend, Ron Douglas, who called 911 at 6:20 a.m. As the responding officers were taking Birgen out of the home, they heard a gunshot. The police found Brynn, dead from a single shot in the head, in the bedroom with her husband.

Friends of Hartman’s, including SNL cohort Jon Lovitz, were understandably distraught. A visibly shaken Lovitz cried at a gathering hours after the news. “I don’t understand how this could happen,” he said.

In the days that followed, Simpsons creator Matt Groening retired Hartman’s characters from the show to honor his friend’s legacy. Saturday Night Live aired a tribute to Hartman, featuring his greatest sketches. Hartman’s best bits included such characters as Bill Clinton, Donald Trump, Frank Sinatra, Jack Nicholson, Ed McMahon, Frankenstein’s monster, and Unfrozen Caveman Lawyer. Hartman won an Emmy for his writing on the show, where he worked alongside Lovitz, Dana Carvey, Dennis Miller, Jan Hooks, Chris Rock, Chris Farley, Mike Myers, David Spade, Sarah Silverman, and Adam Sandler — who called consummate-pro Hartman “the Glue,” for holding the show together through multiple transitions.

Watch: Phil Hartman’s SNL audition:

Gremlins director Joe Dante, who worked with Hartman on what would be his final movie, Small Soldiers, recalled that his friend was content before his death.

“I have a plane. I have a boat. I have a great house. I have a great family. In fact, I have everything I ever wanted,” Dante recounted Hartman telling him, per the Los Angeles Times. “It feels great.”

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