Got Change? The Stories of the Most Generous Celebrity Tippers

Tipping is an important part of social etiquette in many parts of the world. Some people, however, exceed expectations with a mind-blowing show of generosity, and the lucky recipient is left with a lavish – sometimes life-changing – reward for their service. We’ve searched the internet and uncovered the most generous tips of all time – check them out.

Bill’s Creativity Wasn’t Camouflaged

Bill Murray gets extra points for creativity for this “tip”. In 2012, he asked a Philadelphia waitress offhandedly if she wanted anything “from the army-navy store” before leaving.


She replied, “Yeah, camo pants,” and thought nothing more of it. Twenty minutes later, a pair of camo pants were delivered to the restaurant.

Life Tips as an Added Bonus

Actor Bill Murray strikes again – he once left a New York City waiter a US$72 (120%) tip on a US$60 bill, which is a pretty lovely thing to do.


Apparently, he also imparted a brief lesson on how to juice lemons more effectively! With a combined financial tip and life tip, you can’t go wrong.

Swiftly Heading to Chipotle

Pop singer Taylor Swift doesn’t need a restaurant to be generous – in 2014, she reportedly gave US$90 to a fan in New York City when she told Swift she was headed to Chipotle.


Maybe Swift’s a huge fan of Chipotle or maybe the fan just looked really hungry – either way, it’s pretty generous, and we bet that was the best Chipotle the fan’s ever had!

US $96.25 for Your Trouble

We’ve all been there – you arrive somewhere and realize you’ve forgotten all your cash. Well, it happened to actress Charlize Theron in Hollywood in 2014, when she couldn’t pay her US $3.75 bill in Pinkberry.


She promised an employee she would return and kept her word, handing over US $100 and telling the staff to keep the change for their trouble.

When Life Hands You Lemons

A few years ago, Kylie Jenner was cruising around LA with her long-time friend, Anastasia “Stassie” Karanikolaou, when they purchased a glass of lemonade from a stand, tipping US $100.


The whole thing was caught on Snapchat – in true Kardashian/Jenner style – and they drove off after telling the proprietor they “loved” her!

The Most Expensive Eggs in the World

According to Page Six, former “Daily Show” host Jon Stewart left a US 105$ tip for a simple breakfast of coffee and eggs while dining at Junior’s in Times Square.


It may not be one of the biggest tips on this list, but it sure makes for an expensive bite to eat in the morning!

To Have Game or Not to Have Game

When rapper The Game went for a meal at Capitale Grille in West, he proudly tweeted a photo of waiter Eme Ikuakor holding a large wad of cash.


Claiming he left a US$6,000 tip, part of the rambling caption read “My HEART made me do it.” Upon investigation by TMZ, however, it turns out the actual amount was US $250.

Adding a Personal Touch

Jessica Simpson clearly likes to personalize her generosity. In 2011, she left the waitress at New York City’s Lavo a US $300 tip on a US $500 check, which in itself is kind enough.

Source: Pinterest

But she didn’t stop there – with it was a note reading: “You were amazing and make this world a better place. Love, Jess.”

Shaken Up by Miss Jo

CeCe Bruce, a waitress at an Indianapolis Steak ‘n Shake, couldn’t believe her luck when a regular customer, identified as “Miss Jo,” added US$446 dollars to her US$5.97 meal.


Bruce initially declined the tip, but Miss Jo insisted, saying, “You need to take it.” The restaurant’s general manager described Bruce as a great employee that deserved every penny.

Waiting to Make It Big

Amy Schumer used to wait tables before she was famous, and back in 2015, she left a US $500 tip on a US $50 bill in Long Island after finding out her waitress was working two jobs to pay for college.


It’s not every day celebrities act so selflessly, and we’re sure it helped the waitress out a lot. Credit to Amy for not forgetting her life before fame!

Staying Up Pays Off

While on tour with his New Kids on the Block bandmates, Donnie Wahlberg stopped in for a late-night meal at the Waffle House in Edgewood, Maryland—and left the overnight staff a US$500 tip.


It was intended for the three workers to split, and the receipt shows the star’s handwritten tip added to the US$62.75 bill.

Dishing Out Five Big Ones

Kristen Ruggiero, who worked at Uncle Tony’s Pizza and Pasta in Providence, Rhode Island, was the lucky recipient of a US$458 tip for a US$42 check. At first, she thought it was a mistake.


But the middle-aged couple that left the five US$100 bills disappeared before she could ask. One month later, however, they returned to confirm it was left on purpose.

Swiftly Sending an Exclusive Invitation

This is Taylor Swift’s second tip that is generous enough to feature on this list. This time, she left US$500 on a bill at a restaurant in Philadelphia in 2013 but went one step further than usual.


The head chef obviously impressed the singer, as she left him two tickets to her show the following night. That’s something to put on your résumé!

What a Good Girl

Taylor Swift strikes again – this time, in Ralph’s Italian Market in Philadelphia, where she went for a late-night dinner after a Friday night show.


She had obviously worked up an appetite, as she racked up a US$800 bill – but she dropped a US$500 tip, proving herself to be a good girl after all.

How to Honor Your Friend

In 2012, when Shea Mower died in a DUI crash in Indiana, his friends honored his death with a wonderful display of generosity when they celebrated what would have been his 34th birthday at an Outback Steakhouse.


Their tip, a generous US $500 in Shea’s name, went to their surprised server, Cassie Smith, who was, unsurprisingly, overjoyed.

A Truly Awesome Tip

Before 30-year old Aaron Collins passed away unexpectedly, he left instructions for his family: “Leave an awesome tip (and I don’t mean 25%. I mean US$500 on a f***ing pizza).”


His family raised the money to grant their son’s last wish … and then some. Donations poured, and an interactive map with video shows the different places US$500 tips have been left in Aaron’s name.

Not all Heroes are in Movies

Russell Crowe doesn’t just play heroes in Hollywood movies, as demonstrated in 2009 when he brought nine friends to a Welsh pub at the Carew Inn for mussels and chicken.


The bill came to £240 (approximately US$315) but he left a £600 (approximately US$787) tip for the waiters. Last but certainly not least, he and his band performed an impromptu show for local patrons.

Bend it or Tip Like Beckham?

In 2012, when world-renowned footballer David Beckham went to a bar in Culver City, California, he ran up a US $100 tab.

Source: Pinterest

Nothing unusual, you might think. But strangely, he decided to add a zero to that number. The result? A US $900 tip! We’re not sure about “bending it”, but we wish everyone tipped like Beckham!

Drinks are on Amy

This is comedian and actress Amy Schumer’s second generous tip featured on this list. Recently, she left a bartender at popular Broadway musical Hamilton a US$1,000 tip on a US$77 bill.


Hopefully, that was just her unwavering generosity and not as a result of one too many drinks! Either way, we bet the bartender was counting their blessings.

Knight in Sheen-ing Armor

In 2014, a few weeks after Philadelphia Eagles running back LeSean McCoy was accused of tipping a Philadelphia waiter 20 cents, Charlie Sheen came to the rescue.


The actor pledged US $1,000 to the same waiter, Rob Knelly – and he actually did it. We bet Knelly’s not so angry at McCoy anymore!

A Random Act of Kindness

One anonymous customer of a diner in Texas began talking to his waitress and learned of her desire to visit Italy to see her family, having never been able to do so before.


When he told her to “take care” and left, the last thing she was expecting was a US $1,000 tip on a US $60 bill – finally, she was able to take that dream trip.

A Tip Worth Converting For

Rev. Steve Markle conducted a sermon about generosity, and so inspired were the 500+ congregants that they decided to order a pizza and take up a collection plate for the delivery driver.


When the driver arrived at the Sycamore Creek Church in Pickerington, Ohio, she was brought on stage with the pizza and offered the mind-blowing US $1,000 tip! Need any more pizzas, guys?

Cheering for the Home Team

Model Chrissy Teigen and her family dined at a Centerville, Ohio, Outback Steakhouse while they were in town to watch husband John Legend’s high school football team play.


According to their waitress, Mikayla Scott, they left the generous US $1,000 tip – we bet everyone working at the Outback Steakhouse is hoping the high school football team play again soon!

God Bless the Cheddar’s Worker

Khadijah Muhammad, a waitress in Knoxville, Tennessee, was having a rough time in 2014. She had lost her mother and was threatening to have her electricity cut off, so she was working extra shifts at Cheddar’s.


That’s when she received a tip, accompanied by a note saying, “God Bless!”, for US $1,075 on a US $29.30 bill.

A Lesson to Get Involved in

In 2014, an order came into Domino’s Pizza from Indiana Wesleyan University for two pizzas totaling US $12.50. The delivery guy, James Gilpin, was in for a surprise.


He was ushered on stage in a campus chapel filled with 3,000 students and given a US $1,680.86 tip, US $70 in gift cards, and inspirational notes from the students. Why? It was all part of the speaker’s lesson on the act of giving.

Pirates of the Steak House

One notoriously generous celebrity tipper is Johnny Depp, who is known to treat workers well. One of his most generous gratuities was to Mohammed A. Sekhani, a long-time waiter at Gibson’s, a famous Chicago steak house.


One evening in 2009, after Depp and a group of friends left a private room at 2:30 a.m., “Mo” received a hearty US $4,000 tip!

A New Set of Wheels

Greg Rubar, a Houston waiter at D’Amico’s Italian Market Cafe, had his car destroyed by a severe thunderstorm and was, consequently, in financial difficulty.


His lucky day came on 26 May 2012 when a couple who were regulars at the restaurant gave him a US $5,000 tip on a US $26 bill. Rubar used the money to immediately replace his car.

A Dr. a Day Keeps the Financial Advisor Away

Rap icon Dr. Dre, who had just become a billionaire thanks to his Beats headphones empire, left the whopping US $5,000 tip at West Hollywood’s Skybar in June 2014.


Earlier that month, he bought Gisele and Tom Brady’s house for US$40 million, so we think it’s safe to say Dr. Dre had a pretty good month.

Rewards for Being Happy

One day, two customers walked into Cracker Barrel and asked to be served by the grumpiest waiter. Told there were none, they were seated in Abigail Sailor’s section as she was deemed the happiest.


Learning about her tumultuous upbringing, the pair wrote her two checks: US$5,000 for tuition and US $1,000 for supplies. He also left a US$100 tip for good measure, which Sailor split with a coworker.

Becky with the Big Tip

The life of a 20-year-old Pizza Hut employee in Angola, Indiana, was drastically changed when she received a US $10,000 tip from a regular customer known only as “Becky”.


Becky received a large insurance payout after her husband and daughter were killed in an accident and kindly decided to use some of the money to help waitress Jessica Osborne, who had recently dropped out of college due to financial difficulties.

Mystery Visit from the Beast

According to a news report, a man walked into a restaurant in North Carolina, had a few sips from a glass of water, and then proceeded to tip the waitress US $10,000 in cash before leaving.

Source: Instagram

This is probably one of the strangest tip stories – especially as it turns out that the man was none other than Youtube star Mr. Beast.

A “To-Go” Box Full of Surprises

Waitress Stacy Knutson was surprised when a customer left US $12,000 in cash inside a “to go” box. She reported it to the police, who told her she could keep the money if no one claimed it within 60 days.


Sixty days later, Knutson was told the money was part of a drug investigation because the money had “a strong odor of marijuana.” She filed a lawsuit, eventually winning the right to keep this giant “tip.”

Driving for Good Service

Not everyone carries cash these days, so some tips come in unusual forms. One Waffle House Waitress from Georgia has all her Christmases come at once when she received a Dodge Durango!


Yes, you read that correctly. The tip came from one of her regular customers and was completely out of the blue. Talk about driving for good service!

Tuition is on Me

Benjamin Olewine’s bill was only US $3.45. However, that didn’t stop the 92-year-old regular patron from tipping Melissa Mainer almost 5,800 times that, taking an opportunity to share his wealth.


Olewine paid off all Mainer’s tuition bills, which amounted to approximately US $20,000. Mainer is currently a debt-free registered nurse thanks to her kind-hearted benefactor.

Looking for a New Card Dealer, Charles?

When Charles Barkley won US $700,000 in a game of blackjack, he generously splurged US $25,000 of his winnings on a tip for the dealer.


“I think it’s important when you’re successful [to be a good tipper],” Barkley told Conan O’Brien in 2014. “I probably should have tipped more.” We wouldn’t turn our noses up at that!

Paris in New York City

In September of 2014, in New York City bar Marquee, Paris Hilton racked up a bar tab totaling the staggering US $230,000 after ordering giant bottles of Ace of Spades Champagne, and 11 bottles each of Patrón, Cristal, and Grey Goose.


Paris left an approximate 20% tip, which ended up equating to a grand total of US $47,000.

20% of a Lot is … a Lot

Jay Z really pushed the boat – or should we say, champagne bucket – when he made the waitstaff’s night at Miami’s Fontainebleau in 2011.


During his “Watch the Throne” release party, he spent US $250,000 on champagne before leaving a staggering US $50,000 tip. Guess you have to be prepared to tip big if you want to spend big …

The Luckiest Day at Work

In 1995 in Toronto, 24-year-old waitress Tracey Dalton’s life changed forever. Fifty-five-year-old John Steele, a customer, left a lottery ticket as a tip, saying they’d share it if they won.

Source: Imgur

The ticket ended up winning US$184,700, meaning Dalton scored a US$92,350 tip. That’s what we call a great day at work!

Never-Ending Stream of Luck

While not exactly intentional, a man from Denver, Colorado, ended up tipping the huge US $140,000 for an Uber ride. After his driver dropped him off, the man tipped by handing the driver a US $5 scratch card as a tip.

Source: Colorado lottery

The driver won US $30 from the ticket and decided to buy more scratch cards with his winnings. To his surprise, his luck didn’t end. Eventually, the winnings totaled US $140,000!

It Could Happen to You

In 1984 at Sal’s Pizzeria in New York, police detective Robert Cunningham asked Phyllis Penzo to split potential winnings on a lottery ticket instead of receiving a tip. She agreed and helped pick three of the six numbers.


Incredibly, that US$1 ticket won US$6 million, which was evenly split between the two, and a film was made about the incredible story.