Living Large: Times When Celebrities Left Very Generous Tips

Anyone that goes out to eat in the U.S. knows that part of the experience includes giving the server a tip at the end of the meal. While there are many discussions and arguments regarding what the right amount is, most people agree that if you’ve received pleasant or even exceptional service, you can give above the standard value of a tip. Anytime a celebrity visits a restaurant, they attract a significant amount of attention, and whether it’s fair or not, there is also extra scrutiny when it comes to how much they tip, as most celebrities are also quite wealthy. While there have been some less than flattering stories of celebrities leaving a poor tip or none at all, these celebrities went way above and beyond and gave their servers a seriously generous tip.

Donnie Wahlberg

A trend that was quite popular during that year, the 2020 Tip Challenge had a lot of people leaving tips of $20.20 on small bills, but Donnie Wahlberg truly took things to the next level when he left a $2020 tip on a bill of $78.45. He left a nice message that read “Happy New Year, 2020 Tip Challenge,” as well as a nice smiley face. We’re sure this tip left a smile on his sever’s face!

Russell Crowe

While dining at Carew Inn, located in Wales, in 2009, actor Russell Crowe enjoyed chicken and mussels along with the rest of his party. While the final bill came out to $313, Crowe decided to leave an additional $783 tip for the waiters that had served them. They even apparently engaged in a bit of karaoke, which we’re sure was fun for everyone to witness.

Naomi Campbell

On one evening, iconic model Naomi Campbell was dining in London with fellow superstar actress Cameron Diaz. The two decided to head to a bar after dinner, and their waitress was absolutely “shocked” when they left her a tip of $9200. She said that she was so “stunned” by this that she couldn’t fully process it at the time.

Amy Schumer

Since comedian and actress Amy Schumer once worked as a waitress, she remembers exactly what it is like, and she makes sure to tip her servers accordingly. One time she visited Peter’s Clam Bar in Long Island, and was given a bill of $49. She decided to leave a tip of $500, especially after she found out that her waiter Ryan was a student that was balancing two jobs on top of his studies.

John Travolta

John Travolta is a highly recognized actor, and so the fact that he is known to be a great tipper at restaurants is quite helpful for his reputation. In 2012, he was out at a restaurant and was left with a bill of $382.69, on which he decided to give a tip of $100, which is more than the expected $76 that many others would leave.

Taylor Swift

Taylor Swift is known for her generous acts, whether it’s towards her fans, her tour crew members, and also waiters at restaurants. One time in 2013 while she was in Philadelphia she attended Ralph’s Italian Market for a late night feast. The final bill came out to $800, and the iconic singer decided to leave $500 as a tip. While she never posted about it, the grateful waiters made it known.

Charlize Theron

In 2014, Charlize Theron decided it was time for a nice cold frozen yogurt while she was out in Hollywood, so she went to a PinkBerry. When she got to the register, she realized that she didn’t have her wallet on her, but the employees decided to let her have the dessert anyways. Theron was so grateful, that an hour later she returned with her wallet and came back and gave the workers a $100 bill. Since the yogurt itself was $4, it means she left them a $96 tip!

Chrissy Teigen

It’s not every day when a famous model walks into your restaurant. However, waitress Mikayla Scott was working her shift at the Outback Steakhouse in Centerville, Ohio when Chrissy Teigen walked in. While the final bill came out to just under $200, the model left an astounding $1000 tip, which Scott said she shared with her co-workers but her share helped her pay to fix her car. Apparently the model was in town with her husband, who is actually originally from the area.

Post Malone

Rapper Post Malone is known to be quite friendly, and one time when he attended Mel’s Drive-In on Sunset Boulevard in Hollywood, he was very down to earth and spent a lot of time speaking with the employees there. They also shared that when he was finished eating, he left them a huge tip of $1000, and he also took pictures with fans there.

Tom Selleck

Tom Selleck is a legendary actor known for many rules including Magnum P.I. and more recently, Bluebloods. He is another celebrity who decided to partake in the 2020 Tip Challenge. While dining at Elio’s in the Upper East Side of New York City, his final bill came out to $204.68, but he decided to tip $2020 on top of that. He also left a kind note to the staff who served him, saying that he was inspired by Donnie Wahlberg.

Brad Pitt

Once when Brad Pitt was visiting Germany, he was out for a meal and he ended up with a bill that came out to a whopping $1000. He must have truly enjoyed his meal as well as the service he was provided with, because he left a tip of $700, which is a 70% tip!

Harry Styles

Harry Styles had clearly heard about the 2020 Tip Challenge as well because while he was dining at Caribbean Fish Market/Sangrias while in Anguilla, he decided to leave a $2020 tip on his final bill of $472. He was actually dining with Adele and James Corden, and so the waitstaff there were not only greeted with multiple celebrities, but also a generous tip.

Charles Barkley

NBA star Charles Buckley is known to divide people, but whether you love him or not, you have to give him credit where credit it due. He’s known for tipping well, and he shared a story of one time when he won $700,000 during a game of blackjack. He decided to give his dealer a tip of $25,000, and even said that he regretted not tipping him even more.

Shaquille O’Neal

NBA legend Shaquille O’Neal is known for his generosity, and especially for leaving very large tips. He even asks the waiters how much they’d like as a tip, and one time a waitress asked him for $4000, which would cover two months of rent for her. He quickly complied, telling her “okay, no problem,” making her day (and two months!).

David Beckham

Soccer superstar David Beckham is known for being quite friendly, and in 2012, while he was in a Culver City, California, bar with some friends, the final tab came out to be about $100. While paying, he added another zero to the number, meaning he left a whopping $900 tip for the staff.

Jim Carrey

While Jim Carrey is often a mysterious figure in Hollywood, he is known to be very kind towards waiters and for leaving very large tips. Once while he was out at Chester, a restaurant in the Meatpacking district in New York City in 2016, his final bill came out to $151. He decided to leave a tip of $225.

Rihanna

Once time when Rihanna was at fancy bar The Lodge in Austin, Texas, she enjoyed Coke and Jamesons with her friends starting from 1am until the bar closed down. They were grateful for the staff taking such good care of them that Rihanna left a $200 tip on the final bill of $82.25.

Mick Jagger

Rock star legend Mick Jagger is known for his signature dance moves and outlandish outfits, but he is also known as a generous tipper. While visiting Philippe Chow in New York City in 2016, he ordered lavishly and ended up with a bill that came out to $478. While many people tip 20-25%, Jagger left a $500 tip, which was larger than the amount of the entire bill!

Gregg Popovich

Gregg Popovich is the president and head coach for the San Antonio Spurs, and is considered to be one of the greatest coaches of all time. While in Memphis after his team lost to theirs, he was still as generous as ever. He ended up with a bill of $815.73 while dining at McEwan’s, he left the waiters a tip of $5000! Popovich didn’t publicize this, but the server decided to share his kind deed on Reddit.

Dana White

President of the Ultimate Fighting Championship (UFC) is quite the successful businessman, with an estimated net worth of $500 million. With that, he is known to be quite generous. One time he was dining at Empire Asian Restaurant & Lounge in Boston, and he ended up with a bill of $1500. He decided to leave a massive $4000 tip, which completely blew away the restaurant’s staff.

Jessica Simpson

Jessica Simpson is quite the talented businesswoman, earning her fortune through her singing and acting career but also her many business ventures, including in her skincare line, shoe line, and fashion businesses. While dining at restaurant Lavo in New York City, Simpson left a $300 tip on a bill that came out to $500. She also left a kind note to her waitress that read: [thank you for ] “mak[ing] this world a better place…Love, Jess.”

Drew Barrymore

Actress and TV host Drew Barrymore is known to be very generous when it comes to tipping, which was confirmed by actress Anna Ortiz. Ortiz was actually once Barrymore’s waitress, and she shared a story of when Barrymore dined at her place of work, she left her a tip that was twice the bill’s amount.

Tyler Perry

In 2017, Tyler Perry visited a restaurant in San Antonio, Texas, and although his bill came out to just $27, he left a huge tip of $500. He also did not post about his generosity, but the husband of waitress who was tipped decided to share a post about it online. He shared that the money “couldn’t have [come] at a better time” and that Perry’s kindness was greatly appreciated.

Gabriel Iglesias

Comedian Gabriel Iglesias showed up at Gotham Comedy Club in New York City in 2020 for a surprise set, and his show ended up being two hours long. Since this was not an expected show, staff had to stay later at the club than they thought, and Iglesias decided to give them a $3000 tip to split amongst themselves for the extra work they had to do.

Dr. Dre

One time, Dr. Dre was visiting Skybar in the Hollywood Hills. He ordered several shots, and the waitress who served them to Dr. Dre said that they couldn’t have added up to more than $100. However, he stilled gave an astounding tip of $5000 that night.

Ethan Hawke

Ethan Hawke was known for frequenting a particular Thai restaurant in New York City, and he became friendly with the staff after so many visits. Martina Neumann, who worked there at the time shared: “It became so common that I hardly gave pause when I saw him. One night, I was exhausted from two doubles in a row. […] I yawned and opened my eyes to see Ethan Hawke disco dancing, Stayin’ Alive-style. He danced right up to me, pointing his finger and all. I just stared at him and nodded.”

Bill Murray

Bill Murray is known for randomly showing up to weddings and bars, basically crashing events, and since he is a celebrity, most people are pretty excited about it. It also helps that he is known to be generous when it comes to tipping. Once when he was at a place near his home, the waitress there shared that although he and his brother showed up close to closing time, they were so fun and left a 120% tip on a $60 bill that it made it well worth it.

Mark Chesnutt

Mark Chesnutt, who is known for singing “Bubba Shot the Jukebox,” he also has been known for being generous while out to dine. Once while having a meal at a Texas restaurant, a waiter prevented people from bothering him for autographs, and Chesnutt was so grateful that he left a $200 tip on his $100 bill, also telling the manager on duty how much he appreciated his waiter.

Keanu Reeves

Keanu Reeves has a reputation for being very down to earth and friendly. A waiter at a Los Angeles restaurant shared that Reeves attended the restaurant with several people and was very polite and humble throughout their interactions. At the end of the meal, Reeves picked up the bill and paid for everyone and also left a generous tip.

Kelly Ripa

Talk show host Kelly Ripa went on a cruise, and the waiter who served her onboard, named Josh, shared that she was very “sweet” and that she would tip $20 each time a waiter or butler would come to her suite for anything. Josh also said that she tipped the main butler $500.

Chad “Ochocinco” Johnson

Chad Johnson, also known as “Ochocinco,” is quite the character, and is known for being very joyful and positive. In 2022, he left a huge tip while dining at a Greensboro, North Carolina restaurant. His bill was just $24.39, but he left a $1000 tip while at Stephanie’s, with a note that read: “I once scored 6 touchdowns in Madden using myself.”

Burt Reynolds

One time, the late Burt Reynolds attended a restaurant in Fort Worth, Texas with a group of friends. He asked his waiter a serious question, and since the waiter gave his honest opinion, Reynolds appreciated this and gave the waiter a $200 tip as a thank you for his thoughts. In addition to that, he also tipped 50% and gave a Cuban cigar to the waiter at the end of the meal.

50 Cent

One time, rapper 50 Cent went to a Burger King drive through in Queens, New York with social media star Jay Mazini in 2020. Since fast food workers were having a tough year due to the pandemic, they gave out $30,000 in cash to the workers, who were absolutely stunned, especially since their order was just about $15 total.

Jimmy Fallon

The Tonight Show host Jimmy Fallon attended Kissaki Sushi in Water Mill, New York with his wife. He left a $400 tip there, and a fan shared on her Instagram story that not only did they enjoy “amazing sushi and service,” but they also were able to “dine next to” Jimmy Fallon.

Jay-Z

One time, rapper Jay-Z attended Miami’s famous Fountainbleau nightclub in order to celebrate the release of his album Watch the Throne. There, he spent $250,000 just on champagne, including a bottle of Armand de Brignac, which is one of the most expensive bottles in the world. At the end, he left an astounding tip of $50,000 on the exorbitant final bill.

Nev Schulman

Nev Schulman is best known for being the host of MTV’s Catfish. Once while he was at the Denver International Airport, he was ordering some food at Smashburger, and he noticed that his waitress Zulia Reyes was pregnant. Reyes shared that he was very kind and asked her when she was due. When she told him her due date of September 26th, he replied that it was coincidentally his birthday. At the end, when he gave her the check, she saw that he tipped her $926, inspired by his birthday and her due date, writing a note on the receipt that read: “Congrats on your baby girl!”

Jon Stewart

Jon Stewart visited Junior’s in New York City and ordered some coffee and eggs, which couldn’t have cost more than $20 at most. However, according to Page Six, the comedian and TV host left a $105 tip at the end of his meal.

Johnny Depp

Johnny Depp loves to visit Gibson’s Steakhouse in Chicago whenever he is in town. One time he was there with the cast of his film Public Enemies, and although it was very late, the restaurant stayed open late. When the bill came, Depp paid the $4400 total, and on top of that, he gave his waiter Mohammaed A. Sekhani an additional $4000 tip as a thank you for staying open late.

Charlie Sheen

While Charlie Sheen has had his ups and downs, he has known to be generous on at least one occasion. While dining at Philadelphia burger joint PYT, he heard that a waiter was completely stiffed by another well-known customer who gave just 20 cents, he decided to make up for it, tipping waiter Rob Knelly $1000.

Ellen DeGeneres

Ellen DeGeneres hosted the 2014 Oscar Awards, and in a well known stunt, she ordered pizza from Big Mama’s & Papa’s Pizzeria directly to the stage. The man who delivered the pizzas was never actually tipped, and when DeGeneres heard about this, she invited him onto her talk show and gave him $1000. It also helped boost the pizzeria’s sales!