67. John Michael Montgomery
Location: Restaurant in Minneapolis
Initial cost: Unknown
Amount added: 2-25%*
John Michael Montgomery, a revered figure in country music, embarked on his journey alongside his brother Eddie, forming Montgomery Gentry. Venturing solo in 1992, his music career flourished, amassing a $20 million net worth through his significant contributions to the genre.
During a visit to a Twin Cities eatery, country music icon John Michael Montgomery showcased his generosity. Arriving with friends on his tour bus, their demeanor was both friendly and polite. Beyond autographing for a hostess, they graciously tipped between 20% and 25%, leaving a lasting impression.