28. Mark Chesnutt
Location: Restaurant in Texas
Initial cost: $200*
Amount added: $100*
Mark Chesnutt, known for ‘Bubba Shot the Jukebox,’ was a country sensation in the 90s with eight albums under Universal Music Group’s Decca and MCA. His honky-tonk sound was omnipresent on country radio, defining the era.
Contrary to his frugal reputation, Mark Chesnutt once left a generous $100 tip on a $200 meal at a Texas restaurant. He ensured his waiter, Jack, received praise from the manager, dispelling myths about his tipping habits.