Alexis Gilliland
1980, 1983, 1984, and 1985 Hugo Winner for Best Fan Artist
Gilliland is better known as an author than a cartoonist. He won the John W. Campbell award in 1982 for best new author. Oddly enough for someone who won four times there wasn't a lot of examples of his work online. The cartoon above comes from a recent issue of File 770, regular winner of the best fanzine Hugo.Victoria Poyser
1981 and 1982 Hugo Winner for Best Fan Artist
Poyser transitioned from fan to professional shortly after winning the Hugo award. She specializes in this similar kind of fantasy artJoan Hanke-Woods
1986 Hugo Winner for Best Fan Artist
Brad Foster
1987, 1988, Tied for 1989, 1992, 1994, and 2008 Hugo Winner for Best Fan Artist
The most recent fan artist winner took the award for the first time two decades ago. He's also the first of the winners this time who has a website. He holds the record for the most fan artist Hugo awards.Diana Gallagher Wu
Tied for 1989 Hugo Winner for Best Fan Artist

She's better known as Diana G. Gallagher and writes licensed novels under that name. Currently her novels are based on Buffy the Vampire Slayer and Charmed. I aknowledge that is not a very good picture but that is the only picture I have been able to find by her online. Her website is only about her writing and there is another Diana Gallagher who is a professional photographer which made searching difficult.