Server's jobs are never easy. They work long hours for low pay only to deal with customers who can never be pleased and leave measly tips. But every now and then a kind customer restores our faith in humanity. Check out these heartwarming stories of the most generous tippers ever including some surprising celebrity run-ins! You won't believe the couple who tipped their waitress more than $10,000 to pay off her student loans!
The Irish Homecoming
Ben Millar, a waiter in Texas, got the surprise of a lifetime after a diner tipped him $750 in order to help him get back home for the holidays2014all the way in Ireland! Ben is originally from Belfast but now lives in Texas with his girlfriend Taryn Keith. Although Ben was simply sharing a tidbit of his life with the customer, the anonymous individual took the story to heart.
He left the massive $750 tip with a note saying, 201cHopefully this can get you back to Ireland for the holidays.201d Ben and his girlfriend Taryn are expecting their first child and plan to use the money to travel to Ben2019s native Ireland in order for his family to be meet his love and his new baby.
Shaq: Bad At Free-throws Great At Generosity
Shaquille O'Neil: Basketball pro, actor...generous tipper? While on Jimmy Kimmel Live, Shaq shared a bit about his tipping habits, saying, "When I'm at restaurants, I am a big tipper. I like to show people my appreciation.201d
He also asks the server how much he should tip them. Once, Shaq asked a young woman how much he should tip her. She definitely did not hold back and told him $4,000. Of course, to Shaq, that2019s a measly amount of money. After she explained she would be using the money for her rent, he agreed and tipped her $4,000. Every server should hope they are lucky enough to have Shaq stop in for a bite to eat!
The Generous Comedian
Amy Schumer has been involved in her fair share of controversies, but she has been labeled one of the most generous celebrities too. After she saw the Broadway show Hamilton for the first time she left a rather generous tip of $80 with a note that said: "I've been there, I get it, you guys are great."
Schumer enjoyed the show so much that she saw it again, but after the second time, she left the bartenders an even bigger tip of $1,000! One of the lucky bartenders working that night posted the photo on Instagram saying, "And then @amyschumer comes into your work and does something amazing."
A Beautiful Tipping Legacy
After watching his best friend work as a waitress to fund her way through school, Aaron Collins was inspired to help those in the service industry. He even included in his will a special request to leave a $500 tip at a restaurant. So when Aaron died unexpectedly at just 30 years old, his family wanted to make sure they fulfilled his wish.
Aaron didn2019t have much money when he passed away so to carry out his last wish, Aaron2019s brother, Seth, started a website asking for donations to carry out his brother2019s dream. The donations poured in, and Seth was able to leave $500 tips at restaurants all around the country.
Treat Yo Self
Tom Haverford and Donna Meagle from NBC's Parks and Rec are known for coining the catchphrase 201cTreat yo self!201d The phrase refers to a day in which the characters indulge in the finer things and encourage others to do the same. It seems as though the make-believe generosity actually extends to the rest of the cast as well.
One server waited on Parks and Rec alums, Rashida Jones and Adam Scott when they were in town to give a speech at a local college. Not only did the server say the famous duo were amazingly nice, but they were also quite generous tipping nearly 40 percent.
The Student Loan Dream Come True
For any college graduate, this story is the stuff dreams are made of! A waitress in Hawaii was surprised to find a $400 tip on a $200 bill, but that was just the beginning. Cayla Chandara was waiting on a couple visiting from Australia when they struck up a conversation. She told them she had originally moved to the island for school but was working two restaurant jobs to support herself and pay her student loans. The couple left her a $400 tip and Chandara was so moved by the gesture that she found the couple's hotel and delivered a thank you card, dessert, and flowers.
The next day, the couple returned to the restaurant to tell her they wanted to pay off her student loans which totaled more than $10,000! They told her in return, that the best thank you is for Chandara to just "be your best possible self." The next generous couple left a $500 tip on a $42 tab.
201cYou Deserved It201d
Sometimes a little bit of kindness and acknowledgment can go a long way. Kristen Ruggiero is a server who has worked at the same restaurant for over fifteen years. She is also a single mother of three children, which is hard enough in and of itself. One day Kristen went about a normal shift when a couple came in to order a pizza, salad and a pitcher of beer.
The bill came to $42, but Kristen was astounded when she found an additional $500 left on the table. Kristen thought that the tip was a mistake and perhaps the couple intended to less. She even set the money aside until the couple again returned to the restaurant. She confronted the couple, attempting to return the money only to be told 201cit was absolutely not a mistake, you deserved it.201d
The Tip Of A Lifetime
One bartender got the deal of a lifetime by not only receiving a generous tip, but a personal Dave Chappelle showing too! The bartender recounted, "I bartended at Dave Chappelle's private birthday party. He kicked everyone out at the end of the night and came back in to have a drink away from his sycophants and assistants." The two struck up a conversation about Breaking Bad and the bartender said he hadn't finished the show yet.
In true Dave fashion, he had to spoil it a little bit. The bartender continued, "He was the coolest except he spoiled the third to last Breaking Bad episode for me by acting it out word for word and dissecting every minute detail." The bartender also said that he left them a $100 dollar bill and delivered in a regular flashy manner, "he took the bill out of his pocket, lifted it above his head then slammed it down on the bar and shouted BAM!!!" Sounds like Dave definitely has a fan for life!
He Fell On Hard Times And Was Gifted A Car
Server Greg Rubar worked at D2019Amico2019s Italian Market Caf00e9 in Houston, Texas for sixteen years. He became friendly with many of the regulars who came in, even serving one couple for nearly a decade. Greg was struggling after losing his vehicle to flooding during a bad storm in the area. As a result, he was relying on taxis and even the restaurant2019s catering truck in order to get to work. One day, Greg2019s decade-long customers came in gave him a large sum of money.
One customer said, 201cI2019m not going to be giving you a tip for a while. Take this money. Go buy yourself a car. 201d Greg was absolutely astounded at the tip and even tried to give the money back, but the couple refused was was adamant that Greg get himself a new car. See the incredible tip model Chrissy Teigen left in the next story.
Chrissy Loves Food2026And Tipping
Chrissy Teigen got her start as a world-famous model and has now added chef, cookbook author, spokesperson, wife to John Legend and mother to their daughter Luna to her resume. She is also a grade-A snark delivering quality content on Twitter. Despite all of Chrissy2019s success, one of the most loveable things about her is that she has remained so down to earth. While visiting her husband John2019s hometown to watch his high school football team, the family visited Outback Steakhouse.
Apparently, Chrissy is borderline obsessed with the 201cBloomin2019 Onion201d appetizer. Needless to say, waitress Mikayla Scott served the table and was quite nervous about waiting on the famous duo. But the couple was very generous and after paying the $193.81 bill left an additional $1,000. See which generous tip inspired a movie next!
The Screen-Worthy Tip
Have you ever seen the movie It Could Happen to You starring Nicolas Cage? Well, it just so happens that the movie comes from a true story of the biggest tip ever. Former police detective Robert Cunningham was a regular at Sal2019s Pizzeria back in the 1970s and 1980s. Waitress Phyllis Penzo was his regular server and worked at the same restaurant for twenty-four years, working six nights a week. Phyliss and
Robert got to know each other pretty well over the years. One day, Robert asked if Phyllis would want to split a lottery ticket with him instead of the tip. Phyllis agreed to the non-orthodox tipping method, even helping Robert pick what numbers to choose. As luck would have it, a few days later Robert called saying that they won $6 million and half of it was hers!
Now Melissa Mainer Is A Debt-Free R.N.
Melissa Mainer was working a regular shift at a Pennsylvania Peachtree Restaurant when she got the tip of a lifetime. Mainer was waiting on 92-year-old Benjamin Olewine when he tipped her an astounding $20,000 on his $3.45 tab.
The two had struck up a conversation and when the quiet millionaire realized Mainer was paying her way through nursing school, he decided he wanted to help by covering her tuition fees. Today, Mainer is a registered nurse with zero debt! Olewine even said he would be happy to help with her graduate school education too.
Kindness + Kindness= One Beautiful Story
Jessica Osborne, a 20-year-old woman who worked at a Pizza Hut in Angola, Indiana, was definitely gifted the tip of a lifetime. Jessica became friendly with a regular customer named Becky who would come in with her family every Friday. Jessica had previously been enrolled in school but had to withdraw from her studies due to her lack of funds.
Becky was all too familiar with difficult times as her husband and daughter were recently killed in a tragic car accident. Becky received a large settlement from the accident and decided to help her friend Jessica at Pizza Hut. Becky gifted her with $10,000 to help Jessica get back in school. Jessica told ABC News, "It's unbelievable. It doesn't happen to people every day. I mean, I work at Pizza Hut!
The Italian Dream Maker
In a random diner somewhere in Texas, a truly remarkable movie-worthy show of generosity took place. A waitress was given the tip of a lifetime by a mystery man whom she had waited on. The waitress2019 daughter then posted the entire encounter on her blog where it immediately went viral. Apparently, the entire situation was a run-of-the-mill customer and server situation.
The waitress shared with the customer that her family was originally from Italy and that she always wanted to visit. And although she had eight years of education in art, she found hard times after a rough divorce and being stuck in a small town. The man left her $1,000 with a note saying that it was for her trip to Italy. He walked out before the waitress even had a chance to thank him.
Big Tipper Bill
Bill Murray is a legendary actor, comedian, and oddball. He's been known to crash random parties across the United States, where he is, of course, welcomed with glee. However, his interesting habits don2019t just apply to random young people parties, he also is apparently quite generous with waiters. One waiter said that in addition to tipping him 120 percent tip on a $60 check he also played teacher.
Apparently, Bill was able to show the waiter a handy trick when it came to lemon wedges. By rolling the lemon on the cutting board before slicing it, it makes for juicer wedge. Maybe the lemon tip will even get the waiter even more juicy tips in the future!
The Steak N2019 Shake Mystery Tipper
Every now and then a person with some extra money to burn likes to use their money for good. Sometimes these people go to a store in order to pay off everyone2019s layaway for the Christmas season, others are simply big tippers at their favorite restaurant. However, not every restaurant has to be a fancy place, sometimes people can2019t help but love a good ol2019 fashioned Steak 'n Shake. For one waitress named CeCe Bruce, her day to have a marvelous tip finally came.
One regular customer, only known as Miss Jo, add an additional $446 dollars to her measly $5.97 bill. Although, CeCe was originally astounded by the sum, even attempting to return it. Miss Jo told her, 201cYou need to take it.201d The restaurant's general manager definitely agreed saying that CeCe Bruce is an excellent employee who definitely deserved the extra money.
Drew2019s Generous Spirit
Drew Barrymore has always had the reputation for being a free spirit, and although she was much wilder in her younger years, she is known to be quite the generous woman. One person who can actually vouch for Drew2019s big-tipping ways is a fellow actress. Actress Ana Ortiz who is known for roles in the show Ugly Betty and more recently The Mindy Project previously worked as a bartender before finally getting her big break as an actress.
Apparently, Ana actually served Drew a time or two over the years. Ana had nothing but great things to say about Drew and said that both times she served the star, she tipped a full 100 percent.
They Honored Their Late Friend By Tipping $500
Shea Mower worked as a server for the better part of his early life and even paid most of his college tuition with tips he earned working at a restaurant. So when he was killed in a DUI car crash, his friends wanted to honor him in a special way. The group decided they wanted to pay it forward by tipping servers who were in a similar situation as Shea had been.
On Shea's birthday, they got dinner at their local Outback Steakhouse and at the end of their meal, tipped their waitress, Cassie Smith, $500. Smith, who has had her share of loss too told Wave News, "It actually kind of hit home because my mom passed away so I kind of can relate to how it feels to lose somebody."
Thanks, Obama!
The 44th President of the United States is another famous face who has been known to be quite generous with tipping. Even before he was elected to the highest office in the country, Barack was spreading kindness to the masses. While still a candidate, he visited a bar called Raleigh Times Bar in Raleigh, North Carolina.
At the time, TMZ said that he only had one beer that came to a whopping $2. However, instead of skimping on the tip, as many people often do, Barack paid with a $20 bill and left the rest for the bartender as a tip.
Game Of Tips
Joe Jonas and Sophie Turner are definitely in the prime of their life, not to mention their careers. However, just because the two are riding high on massive successes doesn2019t mean they treat others poorly. Actually, the two have garnered quite the reputation for being great tippers! In 2016, the pair dined at Empire Asian Restaurant & Lounge.
The restaurant staff went out of their way to accommodate Joe with a TV so he could watch his favorite team 2013 the New York Giants. According to employees, they were extremely satisfied with the fantastic service and left an amazing tip!