5. President Barack Obama - Best Tipper - The Commander and Chief is known to be a great tipper. While in Rochester, New York at Magnolia deli he had a meeting with college students and parents about college affordability. The check for nine people came to $83 with a 20% gratuity of $16.64 attached. The President thought that a bit low and threw $30 more dollars on the bill, making it a 52% tip.