11 Big Celebrity Tippers

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Some of the biggest celebrities in the world have always made an effort to pay it forward and earned reputations as fantastic tippers. Times have been especially tough lately for those in the service industry and some of the biggest names in Hollywood, music, and sports stepped up to make a difference in the lives of individual servers. Whether they’re going above and beyond in a time of crisis or it’s just something they’ve always done, here are some superstars who are famous for their generosity:

Charlize Theron –$96.25

Back in 2014, Charlize Theron stopped a Hollywood PinkBerry to get a mini frozen yogurt, only to realize that she’d forgotten her purse. The unpaid bill was only $3.75, but if the actress didn’t pay, the worker on duty would be forced to cover it herself. Theron promised the employee that she would be back with the money.

The Hollywood star did come back with the $3.25 she owed – plus extra. She paid her debt with $100, and let the employee keep the change.

Chrissy Teigen – $1K

While there might be some debate about the best way to leave a proper tip (Is it always 20%? Before or after tax? Is there a minimum, if the bill is low?) few people tip over 500% on their meal. That’s what Chrissy Teigen did at an Outback Steakhouse in Centerville, Ohio, leaving a $1K tip on a $193.81 bill.

Post Malone – $1K

When Post Malone visited LA’s iconic Mel’s Drive-In, he took the time to hang out with the staff and take pictures with fans that were there, and he also left a massive tip for the diner staff – $1K.

In the past, Post Malone handed out a far more unusual (but potentially even more valuable) tip to his Postmates driver – a CD with his entire unreleased album.

H.E.R. – $1K

This popular singer-songwriter paid her success forward when she was out celebrating her multiple Grammy nominations at Brooklyn Chop Shop House in 2020. She left a 1K tip for the wait staff.

Amy Schumer – $1K

Amy Schumer has a reputation of being an excellent tipper – for example leaving a 1K tip on a $77 bar tab – and it comes from a decade of personal experience.

While she may be a highly successful comedian and actress today, she spent ten years working in the service industry, so she knows exactly what it’s like to rely on tips.

“I feel fine about having money. I take care of my family, my friends,” Schumer explained, to Howard Stern on his Sirius XM show, “I think I might feel guilty about having money if I wasn’t giving. It’s because it does make me feel great and I feel like I have no other choice.”

Donnie Wahlberg – $2,020

Donnie Wahlberg has a history of leaving highly generous tips for wait staff (including a 2K tip a few months before, and another 2K tip back in 2017,) but one of his recent big tips has had an even greater impact than usual – it’s inspiring others to do the same.

In November of 2020, Wahlberg got lunch for $35.27 and left a tip of $2,020. The restaurant posted a picture of the receipt, showing the tip that the actor left, using the hashtag #2020TipChallenge.

Tom Selleck – $2,020

Wahlberg’s Bluebloods costar Tom Selleck picked up the tip challenge and left a $2,020 tip on a $204.68 bill – alongside a heartfelt note for the restaurant staff.

"I found out that my TV Dad Tom Selleck has generously accepted the #2020TipChallenge at Elios Upper East Side! Love ya dad," Wahlberg tweeted.

Harry Styles – $2,020

The #2020 tip challenge also grabbed the attention of Harry Styles. While on vacation in Anguilla with James Corden and Adele, the musician tipped $2,020 on bill for $472.50.

Shaquille O’Neal – $4K

Shaq is a routine big tipper with a unique strategy for getting good service – he lets his servers ask for whatever tip they like at the end of the meal.

"When I’m at restaurants, I like to show people my appreciation. So when they come up to the table, I say, 'The quicker I get my order, the bigger your tip will be.' And then the food will come fast. When we get ready to leave, I’ll ask them, 'What do you want?' And the most someone said was $4,000. And I said, 'OK. No problem.'"

O’Neal said that the young woman who he gave the 4K tip to was extremely appreciative – he had covered two months of her rent.

Dr. Dre – $5K

Dr. Dre was partying at Skybar in Hollywood Hills when he ordered some tequila shots – and then left a 5K tip on the bill for the waitress. She was reportedly, “stunned” by his generosity.

50 Cent – over $30K

For most, a tip is something added on at the end of the meal. For 50 Cent and social media star Jay Mazini, it was the point of going out. In September of 2020, restaurant workers were being hit hard, so the famous pair went to a Burger King drive-thru in Queens, New York to make a difference.

The two handed out stacks of cash to the employees there, totaling over $30K.

Sources: The Real, The Source, The Associated Press, Delish, People Sirius XM, highsnobiety, Slice, Mashable, bleacher report, AceShowbiz