The comedian, whose career took off back in 2003 after he competed on Last Comic Standing (finishing in second place), has long struggled with his weight. When he was just 16 years old, May was in a car accident that left him with 42 broken bones, according to the Sun-Sentinel. That accident was the beginning of May’s serious weight problems. In the months that followed, he gained hundreds of pounds. His highest weight was somewhere around 800 pounds. According to the Tampa Bay Times, May underwent gastric bypass surgery back in 2004. Although he dropped a good amount of weight (approximately 350 pounds), he was still overweight and couldn’t seem to get himself into a healthy weight zone. His goal was to weigh 250 pounds so that he could “buy clothes at the mall.” Unfortunately, May couldn’t get there. May has even used his celebrity in an effort to try to lose weight. He joined the cast of VH1’s Celebrity Fit Club in 2005 and lost 27 pounds. His weight has fluctuated back and forth since then, but he has never gotten down to his goal weight. In recent years, May weighed about 400 pounds, but just last year, he said that he felt “good.” In 2016, May chatted with Pop Goes the News about his life, a year after his now-ex-wife Lahna Turner filed for divorce. He seemed optimistic about his health and even said that he had been losing weight. “I’m fantastic. I’m as good as it gets. I’m actually losing weight for a change. I’m happy for a change. I’m not miserable. Except for [marijuana] I’m substance-free, which, for me, is awesome. My anxiety is being handled without Xanax or [Benzodiazepines],” he told the outlet. May was suffering from pneumonia in recent weeks. He died after going into cardiac arrest on Friday morning. He was just 45 years young.