In an industry often defined by excess, some stars stand out not for what they spend on themselves, but for how they treat others. From quietly doubling bills to leaving life-changing gratuities, a select group of celebrities has built a reputation among restaurant staff for extraordinary generosity. Whether driven by gratitude, empathy, or a desire to give back, their tipping habits have turned ordinary service moments into unforgettable stories.
Taylor Swift
Taylor Swift has earned a reputation as one of the most generous tippers in entertainment, pairing big gratuities with thoughtful, personal gestures. During a 2013 stop in Philadelphia, she dined with her tour crew at Ralph’s Italian Restaurant, where an $800 bill turned into a memorable night for staff when she left a $500 tip, according to Business Insider.
She went even further after learning the head chef’s son, who is on the autism spectrum, was a fan, gifting him two tickets to her concert the next evening so they could attend together. The moment, which took place during her “Red” tour, reflects a broader pattern for Swift, who is frequently noted for leaving sizable tips and treating service workers with a level of care that goes beyond the check.
Donnie Wahlberg
Donnie Wahlberg has become something of a legend among restaurant staff for his outsized tips and consistent generosity. According to sources like The Independent and USA Today, the actor drew widespread attention with his “2020 Tip Challenge,” kicking it off by leaving a $2,020 tip on a modest $75 bill at an IHOP in Illinois on New Year’s Day.
It was not an isolated gesture. Wahlberg has repeatedly left similar tips across the country, including a widely reported $2,000 gratuity at a Waffle House in North Carolina. He often credits his parents’ background in the service industry as the motivation behind these acts, framing his generosity as a way of giving back to workers who are often overlooked.
Jimmy Fallon
Jimmy Fallon has built a reputation for quiet generosity during his restaurant outings, often going beyond standard tipping etiquette. According to People, he made headlines in 2021 after leaving a $400 tip for a server at Kissaki Sushi, a gesture that quickly circulated among industry insiders.
A few years earlier, Fallon reportedly picked up a $1,100 tab for a table of strangers at Il Mulino, simply because they were respectful and allowed him to enjoy his meal undisturbed. These moments have cemented his image as a celebrity who treats dining out as an opportunity to give back as much as indulge.
Charlize Theron
Charlize Theron has long been associated with outsized generosity when it comes to tipping, with stories that border on the unbelievable. According to Business Insider, she reportedly returned to a Pinkberry in Hollywood in 2014 after initially paying without cash, leaving a $100 tip for a yogurt that cost just a few dollars.
In another instance, she was said to have left a $400 gratuity on a $100 bill, reinforcing her reputation as someone who consistently goes far beyond standard tipping norms.
Harry Styles
Harry Styles has also earned a reputation as a standout tipper, combining eye-catching generosity with a low-key, personable demeanor. According to People, he made headlines in early 2020 after leaving a $2,020 tip on a $473 bill while dining with friends at Caribbean Fish Market, even adding a handwritten “Happy New Year!” note to the receipt.
The gesture, part of the broader “2020 Tip Challenge” trend, quickly drew praise from staff and observers alike. Beyond viral moments like this, Styles is frequently described by servers as polite and approachable, reinforcing a pattern of generosity that feels as genuine as it is substantial.
Drew Barrymore
Drew Barrymore has built a reputation as one of Hollywood’s most consistently generous tippers, often going far beyond standard gratuity. According to The Guardian and Yahoo, she is known for leaving tips that match or even exceed the total bill, effectively doubling what she owes as a gesture of appreciation.
That generosity has extended to more high-profile moments as well, including a widely reported $5,000 tip to Verdura in 2020, part of a broader effort to support local businesses. Stories shared by fellow actors and restaurant staff alike paint a consistent picture, with Barrymore treating tipping not as an obligation, but as a meaningful way to give back.
Bill Murray
Bill Murray has long been regarded as one of Hollywood’s most reliably generous and unpredictable tippers, often leaving gratuities that exceed the total bill. According to People, he is known to tip anywhere from 100% to 120%, including a reported instance in New York City where he left a 120% tip on a modest $60 check, along with some offbeat advice for the server.
True to his public persona, Murray’s generosity often comes with a personal touch, whether it is striking up conversations, offering unexpected words of wisdom, or turning a routine shift into a memorable encounter.
Amy Schumer
Amy Schumer has become one of the most talked-about celebrity tippers, known for leaving eye-popping gratuities rooted in personal experience. According to ABC News, the comedian, who previously worked as a waitress and bartender, has said her generosity comes from understanding the grind of service work.
That perspective has translated into headline-making moments, including a $1,000 tip on a $77 tab in Hamilton in 2016 and a $500 tip on an $80 bill at Union Oyster House the following year. In another widely shared instance, she reportedly left $500 on a $50 check for a server juggling multiple jobs to pay for college. Together, these gestures have cemented Schumer’s reputation as someone who uses her platform and her wallet to make a tangible difference for service workers.
Johnny Depp
Johnny Depp has long been associated with extravagant tipping, often leaving amounts that rival the bill itself. According to Mental Floss, one of his most famous gestures dates back to 2009, when he reportedly left a $4,000 tip on a $4,400 check at Gibsons Bar & Steakhouse while filming Public Enemies.
More recently, during a 2022 visit to Varanasi, Depp booked out the entire venue for a lavish meal said to cost around £50,000, once again leaving a substantial tip for staff. Stories from servers consistently describe him as gracious and appreciative, with gratuities often shared among the entire team, reinforcing his reputation as one of the industry’s most generous high-profile diners.
Shaquille O’Neal
Shaquille O’Neal has built a reputation as one of the most generous figures in any dining room he walks into, often turning tipping into a direct and personal exchange. According to Business Insider, the former NBA star is known for asking servers how much they want as a tip, sometimes matching their answer with staggering sums that can reach into the thousands.
In several reported instances, that approach has led to tips as high as $4,000, reinforcing his larger-than-life persona. Beyond individual servers, O’Neal has also been known to cover entire restaurant tabs, with one widely cited occasion totaling more than $25,000. For Shaq, the gesture is less about flash and more about philosophy, using his wealth to reward hard work and treat everyday workers with the same respect he expects in return.