Steve Dickenson was born in a military family and moved a lot from base to base as a kid. He went into the Navy himself, and after that he embarked on a career as a graphic designer and comic artist, studying at the University of Florida. He made his debut in 1984, with the strip 'Bedside Manor', which was syndicated by Medical Features Syndicate. He was a contributing writer on Hank Ketcham's comic 'Dennis the Menace'.
He created the newspaper comic strips 'Dillon' (Tribune Media Services), 'Tar Pit' (King Features, 1993-1994) and 'Nest Heads' (Copley News Service). He has been working extensively with Todd Clark since 1994, and together they created 'Military Brats' for the Air Force Times, and the syndicated comic strips 'My Brother’s Keeper', 'Lola' and 'Retro Geek' for Tribune Media Services. 'Lola' is an independent woman in her late 70s, that was based on Dickenson's aunt. Clark and Dickenson created 'Lola'in 1999, and cooperated until 2008, with Dickenson doing the Sundays.