13 Celebrities Who Gave Massive Tips After Eating Out

Imagine being a waiter or waitress working in a small local restaurant. Suddenly, you encounter a famous actor or musician who's been seated in your section. At best, you assume you'll have a fun little story to tell your friends at the end of your shift. They order, eat, and leave. But it's only after they're gone that you realize they've tipped you a life-changing amount of money — or at least enough to pay a month's rent.

While it's true that some celebrities are better known for embarrassing controversies and diva-like behavior, others take every opportunity to pass on kindness to everyday people. One of the most frequent examples involves celebrities who've made headlines over the years because of generous tips paid when dining out. In many instances, the meal may have cost little more than $30 or $40, but the tips were worth hundreds or even thousands of dollars.

Country-pop music icon Taylor Swift is known for being generous with fans and causes she cares about, so it's no surprise that she's a big tipper. In December 2023, the "Reputation" singer went viral for passing out $100 tips to stunned Gillette Stadium employees. She'd reportedly passed out the large chunk of cash to her suite's food runners after watching fiancé Travis Kelce's Kansas City Chiefs defeat the New England Patriots. 

While one could say the game's outcome influenced Swift's giving mood, there's evidence to support that she's always mindful of service workers and tipping etiquette. She went viral again in February 2025, this time for tipping the Grammy workers. Redditor Whoopsie_Todaysie pointed out that she asked if the workers were allowed to accept tips. "That clearly shows she does this [on the] regular ... She wants to show her appreciation, but ensures she doesn't get them in trouble too. Pretty classy." With a net worth reported as exceeding $1.6 billion and a successful music career, Swift will likely continue to take every opportunity to show her appreciation for hard-working food runners and restaurant staff, who are no doubt grateful for her big tips.

When it comes to huge tips, Donnie Wahlberg certainly has the right stuff. The famous actor and New Kids on the Block member made headlines throughout 2020 thanks to multiple instances of him leaving massive tips that far exceeded the value of the meals he ordered. According to WTHR, after dining at an IHOP in Illinois on New Year's Day, Wahlberg decided to give the server a $2,020 tip. Making this all the more stunning was the fact that the bill totaled about $78. Walhberg's wife, Jenny McCarthy, posted the receipt to Twitter with the caption, "@DonnieWahlberg starting 2020 off like the amazing man he is." In addition to the IHOP hashtag, she also included #2020TipChallenge, suggesting the intention to either create or participate in an ongoing trend of generous tipping behavior.

Wahlberg was determined to see the trend through. In November 2020, he made the news again for a $2,020 tip, this time for a $35 meal he enjoyed at the Marshland Restaurants and Bakery in Sandwich, Massachusetts. When the restaurant gushed about the actor's kind act on Facebook, Wahlberg replied directly, asking, "Who's next?" Regardless of who else was inspired by the tipping trend, it seems the actor has no intention of slowing down when it comes to rewarding restaurant staff.

Thanks to Jason Derulo, one Omaha waiter earned a life-changing amount of money that transformed an ordinary weekend into an unforgettable moment. As reported by KETV in March 2023, a Charleston's employee named Jordan Schaffer was informed he would be serving a party of 18 patrons. Said Shaffer, "I was like, oh, OK, cool. That's always fun to have." But it was only after the group arrived at the West Omaha establishment that he learned he would be serving Derulo, his family, and his business partner. While the waiter admitted to confusion about what Derulo was doing in that part of Nebraska, it turned out that the pop singer had recently purchased a professional stake in a local women's volleyball team.

While some might have found serving such a large party, never mind a celebrity and his entourage, to be truly daunting, Shaffer and his co-workers proved to be more than up to the task. Derulo was impressed with the service and showed his appreciation with a $5,000 tip. Shaffer even shared the moment on TikTok. "I couldn't believe it," said Shaffer, who described the moment as "heart-stopping." "Getting that money just really took a lot of stress out of my life." In addition to splitting Derulo's tip with a co-worker, Shaffer shared that he used the sudden funds to pay off his overdue college tuition.

Some might consider getting a 20% tip on a $200 bill to be a lucky break, but country star Chris Young decided to make things even more special after dining at the 8th Avenue Tiki Bar and Grill in Myrtle Beach, South Carolina. In June 2025, Young was in town to perform during night two of the Carolina Country Music Festival. The event would also feature popular acts like Rascal Flatts, the Beach Boys, and Jelly Roll. Before taking the stage at the event, Young came into the oceanfront bar for a round of drinks. Later, the country star posed with bar staff for a photo that was shared to 8th Avenue Tiki Bar and Grill's official Facebook page. The post caption cheekily reads, "When a country legend walks into your tiki bar... you pour the good stuff." They also thanked Young for "swingin' by" their bar.

Young showed his thanks with a $2,000 tip, which was ultimately split between the three bartenders who served Young that night. There's no doubt that with gestures like that, Young is welcome to come back any time he's in town.

Sometimes a big tip isn't about showing off wealth or helping out wait staff going through a hard time. Instead, it's a lesson in kindness and not judging a book by its cover. That was the case when R&B legend Tamika Scott gave a thoughtful server a very large tip. Scott detailed the incident herself on Instagram. In August 2025, the singer and her daughter stopped into a Juicy Crab restaurant located in Buford, Georgia. The pair waited for minutes to be seated, but were ignored. Finally, a young waitress sat them at a table. As a reward for taking the time to acknowledge them and treat them fairly, Scott gave the young woman a $700 tip.

"I don't look for special privileges," said Scott, "I believe everyone should be treated fairly, no matter their color, sex, or financial status." She clearly hoped her gesture would remind others to be kind and considerate of others, whether that person is famous or not. At the very least, the big tip made one waitress's night, and perhaps served as a key lesson to her co-workers not to be so quick to overlook a customer who's just as deserving of good service as the next person.

Post Malone's massive tip to one dive bar employee in December 2024 was a pleasant reminder that holiday miracles do exist. As Music Mayhem reports, a single mom named Renee Brown found herself working late on Christmas Eve. Instead of being home with her young daughter, Ilaina, she was forced her to be on the job, waitressing at The Railyard in the River Oaks neighborhood of Houston. It was one of two jobs she held down in support of her family. "I was so sad I had to leave my baby girl to go to work," confessed Brown. "Oblivious that God would send me a Christmas miracle."

That "miracle" took the form of Malone, who was in town to perform as part of Beyoncé's halftime show for the Texans-Ravens game. The rapper and artist Shaboozy popped into The Railyard a little after midnight for a bite. The duo were surprised to learn that the establishment and fans had already covered their meal. Touched by the gesture, Malone asked that he be rung up for a $1 charge so that he could leave a tip. He ultimately gave away $20,000, an amount that immediately brought Brown to tears. "It was a very emotional night already being away from home ... trying to process that they were even there." Brown shared she used Malone's generous tip toward her rent and put the rest into savings.

With Johnny Depp, acts of kindness aren't too unusual. After all, the "Pirates of the Caribbean" star was known to surprise children while dressed as beloved character Captain Jack Sparrow. So it shouldn't be too surprising that Depp was capable of making one Chicago waiter's day with a huge tip. In August 2009, the actor was in town for the premiere of his movie "Public Enemies" and stopped by Gibson's Steakhouse for a bite to eat. According to ABC7, Depp and his entourage racked up a bill of about $4,400. Not only did he cover the meal, but Depp also gave waiter Mohammaed Sekhani a hefty $4,000 tip. Sekhani later admitted that he'd seen and served a lot of celebrities over the years, but that Depp's act of generosity helped him to easily stand out from the rest. 

Depp would repeat his big-tipping nature, this time in 2022 during a music tour in the United Kingdom. The star booked an entire Indian restaurant for his tour crew. After eating, Depp reportedly left a $20,000 tip.

Comedian and actress Amy Schumer is someone who managed to make it big, but didn't forget what it took to rise to the top. During an interview with E! News, Schumer shared that she "waited tables for a long time" before she finally broke out in Hollywood. Though it's been years since she scrubbed tables and served guests, the career left a lasting impression on Schumer, especially "when a waiter is sweet and does a good job" when providing service. 

In 2015, Schumer made headlines when she left a $500 tip for a waiter after eating at Peter's Clam Bar on Long Island. Apparently, the young employee shared with the comedien that he was working two separate jobs to pay his way through college. The confession inspired Schumer to leave a generous tip on her $49 meal. It's something that she admitted to doing all the time. "I can't believe it's a news story," said Schumer, "but hey, everybody should tip a lot. That job is hard!"

Although tipping culture is something we're fairly used to in the United States, country singer Zach Bryan was more than happy to bring it to Dublin, Ireland, and surprise one pub employee in a big way. As the Irish Independent details, Bryan was in the capital city to perform and had settled on making The Celt his go-to place for drinking and unwinding in between his sold-out performances. 

According to pub owner Noel Tynan, Bryan frequently took the time to talk with bar staff and get to know them. One of the young pub workers shared in passing that he was working late to cover college fees. Bryan asked if he could help by leaving a nice tip. In the end, he gave €6,000, equal to about $7,000. Not only that, but the country star also gave away two tickets for his weekend show to the children's hospital in Crumlin.

In October 2017, model Chrissy Teigen left a Centerville, Ohio waitress "the biggest tip of her life" after dining at the local Outback Steakhouse. Teigen's husband, singer John Legend, is from the area. He had reportedly returned to his hometown for the high school football game between Kettering Fairmont and Springfield. Waitress Mikayla Scott was at work when Teigen entered the restaurant with an entourage of several people, including her daughter, Luna. 

Although Scott was admittedly nervous about serving the model, she did her best to make things flow smoothly for Teigen and her friends. The effort paid off when Scott found herself rewarded with a $1,000 tip. The stunned waitress said after receiving the generous gift, "I was like, 'Oh my god, praise the Lord." It was a chance encounter that left Scott with the money to repair her family's car. Perhaps out of a combination of gratitude and a desire to pay things forward, the Ohio waitress decided to split a portion of Teigen's tip money with some of her co-workers.

Back in October 2024, Jelly Roll was in Little Rock, Arkansas to perform a sold-out show as part of his "Beautifully Broken" tour. Prior to the show, the hip-hop country artist decided to not only do something awesome for the local community, but also to make the night of Gus's Chicken's staff with a huge tip. 

Jelly Roll took to his official Twitter account to announce that he would be providing free food. "If you come to Gus's Chicken in Little Rock, Arkansas, today, the food is on me, baby." Plenty of people took the artist at his word when he invited them to "come get a free meal." When all was said and done, the surprise meal for fans cost about $11,000. As a show of thanks for their help in making the fun food event a success, Jelly Roll decided to give Gus's Chicken staff a $7,500 tip.

While some celebrities make a big show of their tipping, others prefer to keep their kindness under the radar. That could be why it took an anonymous source to help the public find out about Jimmy Fallon's dining behavior. In January 2021, Page Six published an exclusive story about the "Tonight Show" host sharing a meal with his wife, Nancy Juvonen. The pair reportedly enjoyed a low-key dinner at Kissaki, a Japanese restaurant in the Hamptons not too far from Fallon's Sagaponack home.

According to the source, Fallon left behind a $400 tip, much to the excitement of the man who had waited their table. Even though the COVID-19 pandemic was very much a concern at the time, Fallon, who was masked, reportedly posted up for fans behind plexiglass before heading on his way. The late-night host's behavior is a reminder that you can still be awesome even when no one's watching.

Lady Gaga is a much beloved pop diva for a reason. The singer often goes out of her way to inspire and empower her fans, whether through her music or acts of charity. This behavior also extends to her dining habits, as one happy server revealed on social media. In June 2020, the singer and romantic partner, Michael Polansky, dined out at a restaurant in Malibu. While they had two separate food orders that totaled $61.52, they ended up leaving generous tips. Between them, the server collected about $700. In a since-deleted tweet, the server shared a copy of Gaga's receipt as proof of the order and the tip with the caption, "Turns out Lady Gaga is cool af."

Lady Gaga fans quickly confirmed that the post was legitimate, as they recognized her unique signature. They also teased their favorite artist, noting that her attempt to add up the food total wasn't quite correct. While her math might have been off, the "Abracadabra" singer's sweet gesture more than likely made up for it in the eyes of the waiter and Little Monsters everywhere.