Fleming's professional career began with freelance work from Alfred Hitchcock's Mystery Magazine upon graduation doing black and white illustrations.[2]
In 1991 Fleming landed a full-time position at WWE (known at the time as the WWF) as a costume designer, logo designer, prop creator, and Illustrator. Fleming's artwork for WWE appeared on Wrestlemania T-shirts, VHS covers, and other merchandise items. Fleming made his first impact on pop culture by creating and designing characters for the WWE including Papa Shango, Crush, Adam Bomb, 1-2-3 Kid, and Hall of Famer Razor Ramon.[3] Fleming also designed and created the scepter for the first pay-per-view "King of the Ring" event in 1993.
Fleming returned to freelance in the mid-1990s and has painted trading cards, comic book covers, paperback covers, magazine covers, and posters for companies such as Marvel Comics, DC Comics, Heavy Metal Magazine, Image Comics, Dark Horse Comics, World of Warcraft, Magic the Gathering, White Wolf Publishing, Cracked magazine, and others.
Fleming was chosen by Skybox/DC Comics to paint the "Doomsday" and "Funeral for a Friend" trading card during the legendary "Death of Superman" story line in the 1990s. He produced covers for Marvel featuring Elektra.[1][4]
Fleming is known for Art Nouveau drawings and paintings that have won awards and Chesley Award nominations.
Fleming is the author of Draw & Paint Fantasy Females, published by Impact, an imprint of F+W.[5] It has been translated in three languages (Chinese, Spanish, and German).
Fleming also has done artwork for the film & TV industry including: "Stay Alive" starring Frankie Muniz, "Stateside (film)" starring Val Kilmer, "Surface", and "Life". Fleming was also official artist for The Jodie Foster movie "The Dangerous Lives of Altar Boys"[6]