The annals of Saturday Night Live history have no shortage of tragedy, from assorted drug-related deaths (we’ll never forget you, John Belushi) to the cruel hands of fate extending to seize others before their time as well (you too, Gilda Radner). But among the most heartbreaking was the sad lot of Phil Hartman, an eight-season veteran who kept the show riotous, relevant, and ridiculous during the late ‘80s and early ‘90s. An illustrious career came to a terribly premature close when Hartman’s unstable, lapsed-addict wife Brynn Omdahl shot him in the head during a coke bender and then turned the gun on herself before she could be apprehended by the police. Hartman had been responsible for so much joy and laughter over the years, both in his capacity as SNL’s resident Bill Clinton, as the co-creator of the Pee-Wee Herman character and a writer of the cult classic Pee-Wee’s Big Adventure, and as a regular voice actor on The Simpsons through Lionel Hutz and Troy McClure. But his death brought a career in happiness to a most miserable end.