Guest Stars David Alford as Bucky Dawes Ed Amatrudo as Glenn Goodman Aubrey Peeples as Layla Grant Judith Hoag as Tandy Hampton Oliver Hudson as Jeff Fordham Chaley Rose as Zoey Dalton Melvin Ray Kearney II as Bo Derek Krantz as Brent Ashley Thomas as Jeff's Assistant Samantha Dibiccari as Fan #1 Michaela Allsup as Fan #2 Henry Arnold as AA Speaker Terri James as Dr. Christina Winkler Conan O'Brien as Himself Michael Harding as Mike Katie Cook Pisapia as Herself (CMT Host) John Hamlin as CMT Producer Cinda McCain as Carrie Franklin Rhes Low as Appraiser