| 151 Years | YMCA |
| 132 Years | Ruby Concrete Co |
| 102 Years | R E Moore & Sons, Inc |
| 92 Years | Beshear Funeral Home, Inc |
| Clark Beshear & Clark | |
| 84 Years | The Messenger |
| 80 Years | Barnett-Strother Funeral Home, Inc |
| 79 Years | Riddle Insurance |
| 76 Years | Prow Brothers |
| 74 Years | Madisonville Building & Loan Assn. |
| Ferrell's Snappy Service | |
| 73 Years | Reid-Walters Funeral Home |
| 64 Years | Harris Funeral Home |
| 62 Years | Audibel |
| 61 Years | Period, Inc |
| 54 Years | Fugate Lumber |
| 47 Years | Don Peeler Pharmacy |
| 45 Years | Western Kentucky Glass, Inc |
| 44 Years | Hart Equipment |
| 39 Years 11 Years | Ridgewood Terrace Brown Rest Home |
| 38 Years | Legate's Furniture |
| 36 Years | Merle Norman Cosmetics |
| 35 Years | R & D Electric |
| 34 Years | Big 'B' Cleaners |
| 31 Years | GE Aircraft Engines |
| 29 Years | James W Teague Insurance Agency |
| 28 Years | Arctic Refrigeration |
| Todd's Furniture | |
| Arctic Heating & Air Conditioning | |
| 26 Years | Hanner Machine Co |
| 25 Years | Mike's IGA Foodliner |
| 23 Years | Cumens Lumber |
| 22 Years | Sharkey's Westside Service |
| Tucker's Cafe | |
| James' Jewel Box | |
| Best Western | |
| 21 Years | Bluegrass Pharmacy |
| 19 Years | Carter Plumbing, Heating & Air Conditioning, Inc |
| 17 Years | Domino's Pizza |
| 14 Years | Lacy Tire & Auto |
| Gerda's Ceramics & Porcelain Dolls | |
| Country Cupboard | |
| 10 Years | Bluegrass Fashions |
| Direct Gas & Oil, Inc | |
| Uniform Boutique | |
| 9 Years | On Target [hunting outfitter] |
| 7 Years | Coal Field Carpets |
| 6 Years | Glass-Pac [Livestock & Poultry Equip, Sales, Serv, Repair] |
| 5 1/2 Years | First United Bank |
| 2 Years | BackStreet Music |