With his work at TSR in the 1980s, he is considered one of the artists contributing to fantasy art's "golden age".
"[1] Caldwell took up an interest in painting fantasy and science-fiction art while in junior high school.
"[1] Caldwell earned a fine arts degree at the University of North Carolina at Charlotte, then graduated from the University of North Carolina at Greensboro with a Masters of Fine Arts degree.
"[4] Caldwell gained fame producing work for TSR from 1982 to 1992, illustrating many Dungeons & Dragons products at a time when the game was around the peak of its popularity.
In 2014, Scott Taylor of Black Gate, named Clyde Caldwell as 9C in a list of The Top 10 RPG Artists of the Past 40 Years, saying "Clyde took great advantage of his place and offered up a great deal of sublime and lasting work, although he was never really one to go outside of TSR even after he left the company, although like many he went into covering novels.
"[7] In 2003, a Flash animation slideshow titled Family Art Corner at the Wayback Machine (archived March 9, 2008) was released anonymously, alleging that a woman named Jan McRae had plagiarized the work of many artists, including Caldwell, for reproduction in proselytization tracts printed by the Children of God cult.