Ralphie May, a larger than life stand-up comedian who won the hearts of America if not also their votes in the very first season of NBC’s Last Comic Standing, has died. May was 45.

Though battling pneumonia for the past week, May continued to show up for his 2017 residency at Harrah’s Las Vegas. He had just won Casino Comedian of the Year in an award ceremony on Wednesday. He died of a heart attack early Friday.

Born Feb. 17, 1972, in Chattanooga, Tenn., and raised in Arkansas, May caught a big break while still a teenager, winning a contest to open for Sam Kinison.

May took Kinison’s suggestion to move to Houston to become a professional comedian, and he graduated from the High School for the Performing and Visual Arts there.

When I first saw May, he was the feature act on the road touring with headliner Jay Mohr. May also appeared regularly in sketches on Mohr’s TV sports series in the early 2000s, Mohr Sports. So I wasn’t surprised the following year to see May competing on the first season of Last Comic Standing, hosted by Mohr, nor that May made it all the way to finals. What surprised everybody was watching May perform an emotional set in the finals, only to somehow lose to Dat Phan.

May went on to a lucrative stand-up career, though. He made four stand-up hour specials for Comedy Central, followed by two for Netflix.

He sat down with me and his then-wife, musical comedian Lahna Turner, in the spring of 2015 for what would be Episode #4 of my podcast, Last Things First, where he went into great detail about his life, comedy career, and philosophy. A woman was filming it for a documentary about the couple. I don’t know what happened to that project, as Turner filed for divorce later that year.

One of the last times I saw Ralphie May was in Montreal last summer, where he performed at Just For Laughs and competed on Comedy Central’s inaugural season of Roast Battle. He also told a story for Ari Shaffir’s Comedy Central storytelling series, This Is Not Happening.

Actually, the last time I saw Ralphie, he showed up with a crew at the famous Salt Lick BBQ south of Austin during Moontower while I was waiting to be seated with by comedy buddy Mark. Ralphie was kind and funny to the core, and to the end.

I wish this were not happening, but the news is all too real. Ralphie May is dead at 45. He shall be missed.