Founded in 1998 by Stephen M. Vest,[1] publisher, Michael Embry, editor, (who retired in 2006) and business manager Kay Vest, it featured actor George Clooney on its first (and 101st) cover and has featured such Kentucky notables as Ashley Judd, Molly Sims, Wendell Berry, Silas House, Annie Potts, and numerous others.

Also in 2005, Kentucky Monthly was featured in the Stu Pollard film Keep Your Distance in a scene where the main character is named Kentuckian of the Year.

[2] Winners of Kentucky Monthly's Kentuckian of the Year award include: Miss America 2000 Heather French Henry (1999), who has graced the cover four times, Heath High School-shooting survivor Missy Jenkins (2000), Drs.

Layman Gray and Robert Dowling (2001), First Lady Judi Patton (2002), Kentucky's military (2003), KCTCS President Michael McCall (2004), author Wendell Berry (2005), Drs.

On December 26, 2008, Kentucky Monthly presented the Kentuckian of the Year Award to Riggle at a University of Louisville basketball game.