I worked in the restaurant industry for what felt like 100 years, so stories like this make me smile. I have waited on everyone from Tom Jones to Drew Barrymore... But my most memorable tips have been from Average Joes. One dude knew I had car problem, and needed $300 worth of work; he left me a $300 dollar tip. And once, no joke, a guy bought me a plane ticket to go see Gentleman Caller. (In the beginning of our relationship, he was still in the Navy stationed in Florida.) Random acts of kindness are alive and well.
Dr. Dre just became the richest man in hip-hop—and he's spreading his good fortune around. Last week, the rapper was partying at West Hollywood's Mondrian Hotel, and when he left, he gave his waitress a $5,000 tip. "She was stunned," a source tells Radar. He joins the ranks of these dozen other big celeb tippers:
2. Earlier this month, Charlize Theron got Pinkberry in Hollywood, but didn't have cash to pay her $3.75 bill and promised to return. She came back more than an hour later ... and gave the employee a $100 bill, letting her keep the change, TMZ reports.
3. Last year in a Philadelphia restaurant, Taylor Swift not only left a $500 tip—she also gave the head chef two tickets to her show the next night for his son, a big Swift fan, the New York Daily News reports.
4. Brad Pitt, Angelina Jolie, and their kids ordered $1,000 worth of food at a Japanese restaurant in Berlin last year—nearly everything on the menu—and then left a $846 tip, Entertainmentwise reports.
5. In 2011, Jessica Simpson tipped 60% on a $500 restaurant bill at Lavo in New York, and also left her waitress a note telling her she makes the world "a better place," the Daily News reports.
6. At a Welsh pub in 2009, Russell Crowe left a $1,000 tip on a $400 tab—and played an impromptu set with his band, Hello reports.
7. When Conan O'Brien interviewed him earlier this year, Charles Barkley confirmed the longstanding rumor that he is an amazing tipper, and even once tipped $25,000 after winning $700,000 playing blackjack. "I probably should have tipped more, to be honest with you," he said.
8. Jay Z once spent $250,000 on champagne at a Miami nightclub and then left a $50,000 tip, Radar reports.
9. You might not expect it, but Paris Hilton is reportedly a great tipper, always generous with wait staff, manicurists, valets, and drivers, according to the Miami New Times.
10. In 2008, David Beckham was out celebrating with teammates—all he drank was mineral water, and the bill only came to $100, but he left a $1,000 tip, Hollyscoop reports.
11. Stained Apron keeps a running list, based on intel from servers, of good and bad celebrity tippers. On the nice list: Bill Murray, who reportedly once left an anonymous server a 120% tip on a $60 check.
12. Johnny Depp ran up quite a bill at Gibson's steakhouse in Chicago in 2009, ordering a few $500 bottles of wine. At the end of the night, he left a $4,000 tip, Radar reports.