21. Jessica Simpson

Location: Lavo

Initial cost: $500*

Amount added: $300*

Transitioning from a celebrated pop icon, Jessica Simpson now shines as a fashion industry titan, amassing a $200 million fortune. Not just a success story, she’s also known for her exceptional generosity, particularly towards service staff.

Back in 2011, Simpson’s kindness made headlines when she left a $300 tip on a $500 meal at Lavo, New York. The New York Post shared that she praised her waitress with a heartfelt note, highlighting her positive impact on the world and signing it with affection.