Biggest Tipping Stories in History

Big Tip

Most people have worked in the service industry at one time or another, whether to pay their way through school, a fun summer job, or as a way to make ends meet. Servers and bartenders can make a decent living in the right places, though it is hard work not only physically but psychologically too. Giving service with a smile to people who are rude, obnoxious or abusive is no easy feat. Which is why when stories of awesome tips go viral, it heartens those in the industry that perhaps one day, it really could happen to them.

Johnny Depp at a Chicago Steakhouse


Celebrities can be challenging to wait on, not just because of their personality, but the hordes of people clamoring to see them, get a picture or an autograph. One famous person who is not only humble and kind but a fantastic tipper is Johnny Depp. As if we needed another reason to love this talented, handsome actor, he once left a $4,000 tip to a server at a Chicago steakhouse while filming Public Enemies. His server, Mohammed Sekhani, had waited on many stars before but says that Depp is just a really ‘cool dude’. No doubt after leaving such a generous tip!

Aaron Collins Last Wish

Those who have spent time in the industry and have watched friends struggle alongside to pay school bills or cover this month’s rent tend to want to help their fellow compatriots out when they can. One such man, Aaron Collins, left a directive in his will that he wished his family to leave a deserving server a $500 tip. Sadly, he passed away unexpectedly at age 30 and didn’t leave any money to his family to carry out his wish. To honor his brother, Seth Collins created a website in an effort to raise money to follow through with his brother’s will. An outpouring of love and donations came rolling in, totaling over $66,000. The family has left many $500 tips, all in the memory of Aaron.

America’s Sweetheart Taylor Swift is a Generous Tipper

Taylor Swift is known to most of America as the good girl. Unlike many stars who make it big when they are young (ie Brittany Spears), Swift seems to be holding true to her mid-western upbringing and still charming Americans everyday with her angelic voice. In 2013, she and her friends went to Ralph’s Italian Market for a late night dinner after a show in Philadelphia. The kind-hearted songstress left a generous $500 tip for her server which left her fans smiling and confident that she is still the good girl.


Igniting Faith in Humanity

Greg Rubar served at D’Amico’s, located in Houston, TX for 16 years when he lost his vehicle in a thunderstorm flood. He had been struggling to get to work, taking taxis and using the restaurants catering truck so he could make money for another car. Being the favorite waiter of a local couple, they heard of his plight. When they were paying their bill, they left him a $5,000 tip for a $27 meal telling him to use it for a new car. It is stories like this that give us faith in humanity!

Biggest Tip in History?

Just like in the movies, Detective Robert Cunnigham was eating at his favorite spot, Sal’s Pizzeria and his server, Phyllis Penzo was one he knew well from his frequent visits. One night, he offered to split a lottery ticket with her instead of leaving a tip. She agreed and helped him choose the numbers. Imagine Penzo’s surprise when she got the call from Cunningham that their ticket was worth $6 million and half of it was hers! The film “It could happen to you” starring Nicolas Cage and Bridget Fonda which was released in 1994 was based on Robert Cunnigham and Phyllis Penzo story.



These stories are just a few of hundreds that show not everyone is a tough customer. Be sure to take care of your servers and bartenders – they work hard for those tips!