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2000[]
- February 10 – Jim Varney died, aged 50.
- February 20 – Bernard Hickman died, aged 88.
- March 7 – Pee Wee King died, aged 86.
- June 7 – Historical Marker 2047 - Pawpaw Tree Incident dedicated in Buskirk.
- September 24 – Jerry Claiborne died, aged 72.
- November 20 – Cal Turner died, aged 85.
2001[]
- February 8 – Tony Dunnavant died, aged 46.
- April 28 – James Still died, aged 94.
- May 2 – Altawood Historic District listed on National Register of Historic Places.
- May 2 – George T. Stagg Distillery listed on the National Register of Historic Places.
- June 10 – Historical Marker 2066 - Hog Trial was dedicated in McCarr.
- June 10 – Historical Marker 2068 - Site of Killing of Asa Harmon McCoy was dedicated in Ransom.
- August 1 – Martin Huston died, aged 60.
- September 5 – Cawood Ledford died, aged 75.
- October 7 – Jimmie Logsdon died, aged 79.
- December 20 – Foster Brooks died, aged 89.
- December 22 – Lance Fuller died, aged 73.
2002[]
- January 9 – Bill McCutcheon died, aged 77.
- January 14 – Paintsville UFO and Train Collision
- January 26 – Milt Ticco died, aged 79.
- February 20 – Laura duPont died, aged 52.
- June 29 – Rosemary Clooney died, aged 74.
- August 9 – Marion L. Boswell died, aged 78.
- August 31 – Lionel Hampton died, aged 94.
- September 6 – Berry Mansion listed on National Register of Historic Places.
- September 9 – Gerald W. Johnson died, aged 83.
- October 8 – Henry Ward died, aged 93.
2003[]
- May 1 – Miss Elizabeth died, aged 42.
- May 12 – Bross Townsend died, aged 69.
- August 2 – Redd Stewart died, aged 80.
- August 26 – Thomas Appelman died, aged 68.
- October 1 – Julie Parrish died, aged 62.
- October 14 – Ned Breathitt died, aged 78.
- December 4 – Jace Bugg died, aged 27.
- December 16 – Gary Stewart died, aged 59.
- December 26 – Danny Fargo died, aged 44.
2004[]
- January 18 – Ann Del Farrish died, aged 50.
- January 29 – Louie B. Nunn died, aged 79.
- February 24 – Booker Noe died, aged 74.
- June 7 – Richard E. Bush died, aged 79.
- October 15 – Tex Ritter died, aged 80.
- November 14 – Evelyn West died, aged 83.
- December 16 – Martha Carson died, aged 83.
2005[]
- January 4 – Guy Davenport died, aged 77.
- February 20 – Hunter S. Thompson died, aged 67.
- April 18 – Clarence Gaines died, aged 81.
- June 28 – Thomas D. Clark died, aged 101.
- June 29 – James Gilbert Baker died, aged 90.
- August 8 – Robert A. Baker died, aged 84.
- September 22 – Lee Huber died, aged 86.
- November 16 – Paul Noel died, aged 81.
- December 3 – Herb Moford died, aged 77.
2006[]
- February 3 – Jean Byron died, aged 80.
- February 17 – Gertrude Ganote died, aged 86.
- March 6 – Anne Braden died, aged 81.
- April 3 – Barry Bingham, Jr. died, aged 72.
- July 16 – Malachi Thompson died, aged 56.
- December 11 – Homer Ledford died, aged 79.
- December 29 – Martin Jeff (M.J.) Bannon House listed on National Register of Historic Places.
2007[]
- May 21 – Clark Adams died, aged 37.
- July 3 – Boots Randolph died, aged 80.
- August 23 – William E. McAnulty, Jr. died, aged 59.
- August 31 – Gay Brewer died, aged 75.
- September 7 – Russell E. Doughterty died, aged 86.
- November 29 – Ralph Beard died, aged 79.
- November 29 – Tommy Kron died, aged 64.
- December 2 – Elizabeth Hardwick died, aged 91.
2008[]
- February 25 – Static Major died, aged 33.
- May 11 – Dottie Rambo died, aged 74.
- August 5 – Shelby Linville died, aged 78.
- September 1 – Mel Ignatow died, aged 70.
- October 6 – Larry Belcher died, aged 61.
- October 15 – Jack Narz died, aged 85.
- November 21 – Tom Gish died, aged 82.
2009[]
- January 8 – Don Galloway died, aged 71.
- January 13 – Lanny Kean died, aged 48.
- February 15 – Damon E. Allen died, aged 88.
- February 20 – Theo's Story by Ron Rhody was published.
- March 15 – Billy C. Clark died, aged 80.
- March 17 – Jane Mayhall died, aged 90.
- April 27 – Greg Page died, aged 50.
- May 30 – Jim Rose died, aged 62.
- June 9 – Jack Littrell died, aged 80.
- June 24 – Tim Krekel died, aged 58.
- June 25 – James Baker Hall died, aged 74.
- September 16 – Mary Travers died, aged 72.