9 Amazing Tipping Stories
By Jill Harness
In 2014, a waitress at a Waffle House in North Carolina was given a $1000 tip from a generous customer—but she had to return it due to the restaurant's policy against large gratuities via credit card. But after some light online uproar, the waitress finally got her tip when the customer wrote her a check.
Add this to the list of rare instances when we hear about excessive and genuinely kind tippers. Fortunately, such people are out there.
1. A $500 Tip As A Last Wish
Aaron Collins always felt sympathetic toward those who worked in the service industry after he worked in a pizzeria and watched his best friend put herself through school as a waitress. That’s why he added a stipulation to his will: He asked his family to leave a huge $500 tip at a restaurant. The 30-year-old died unexpectedly in 2012, and because he didn’t leave any money to his relatives to complete this last wish, his brother, Seth, put up a website, aaroncollins.org, to collect donations. What he didn’t anticipate was that the donations would keep coming, allowing Seth Collins to leave $500 tips at restaurants around the country. All of the events are documented on YouTube videos that are linked to on Aaron Collins’s memorial website.
Since the website was set up, the family has collected more than $65,000 and given back over $22,000 in tips. The restaurants are chosen randomly and servers receive the tip no matter how good the quality of service actually is. Of course, while the family enjoys surprising their servers with the amazing tips, they still prefer to have a home-cooked meal on occasion. "Some weeks I may be able to take a break from going out to eat," Seth Collins told ABC News. Even so, the family intends to keep giving out these tips on a weekly basis until the donations are completely expended.
2. The $500 Pizza Dinner
Rhode Islander Kristen Ruggiero was a single mom of three who had had a tough time making ends meet by working the restaurant job she held for more than 15 years. One day, a couple came in and ordered a pizza, a salad, and a pitcher of beer only to settle their $42 bill by leaving $500 on the table. At first, the waitress thought they made a mistake and accidentally left the cash, thinking they were $10 bills. So Ruggiero set the money aside until the pair returned to the restaurant and tried to return it to them. That’s when they assured her that the $458 tip was no mistake. "He said no it was absolutely not a mistake, you deserved it," Ruggiero told WLNE-TV.
Grateful for the tip, Ruggiero took the opportunity to pay off some of her bills and then spent the remainder on a trip to Six Flags with her kids.
3. The $500 Memorial Tip
Shea Mower 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 decided the best way to honor him would be to pay it forward by giving one lucky waitress a $500 tip. The group all chipped in for the tip and on Mower’s birthday, they had dinner at Outback Steakhouse. At the end of the meal, the group donated the entire sum to their waitress.
Prior to their big tip, the group also gave a high school student a $500 scholarship in Mower's memory to raise awareness about drunk driving.
4. The $5000 Tip
Greg Rubar was a waiter at D’Amico’s Italian Market Café in Houston for 16 years and had been waiting on one particular couple at the restaurant for eight years when the customers handed him 50 $100 bills. The man told Rubar, “I’m not going to be giving you a tip for a while. Take this money. Go buy yourself a car. ”
The instructions to buy a car weren’t just random—the couple knew that Rubar had lost his car when it was flooded in a thunderstorm a few weeks before. In fact, the waiter had had to take taxis and borrow his restaurant’s catering truck just to get to and from work.
Greg tried to return the money to the couple, but they refused, insisting he get a car with the cash.
5. Johnny Depp's $4000 Tip
While filming the 2009 drama Public Enemies, Johnny Depp visited Gibson’s steakhouse in Chicago many times and, on one particular evening, he and his group arrived at 11:30 p.m. and stayed for three hours while they ordered bottle after bottle of $500 wine. When they left, Depp left the server a $4000 tip for his efforts.
“I have worked with a lot of stars like Sean Connery and Robert De Niro, but Johnny Depp is my favorite. He is a very soft-spoken guy who is very charming and sweet—when I wait for him he doesn’t like to be too fussed over and is not in any way demanding,” server Mohammed A. Sekhani told Radar Online. “He may be one of the most famous actors in the world but he is a very humble guy and a really cool dude.”
6. The $12,000 Tip
Some servers who receive a $12,000 tip wouldn’t report it to the IRS, let alone turn it in to the police. But Stacy Knutson was a very honest woman, and after customers left her one of the most generous tips in history, she turned it in to the police, worried that it was stolen or tied to some crime. The mother of five was told that she could keep the cash if no one claimed it in 60 days, but after the waiting period ended, officials told her she couldn’t keep it after all because it smelled like marijuana and had been seized under state law. To compensate her for her honesty, police offered her $1000.
Knutson refused the offer and filed suit to get the full sum back. The police quickly changed their minds and returned the full amount.
7. The $3 Million Tip
Here’s one of the most famous tipping stories of all time. In fact, this story eventually became the basis of the movie It Could Happen to You, starring Nicolas Cage.
In 1984, police detective Robert Cunningham had been a regular at Sal’s Pizzeria for eight years. As Phyllis Penzo waited tables there six nights a week for more than a quarter-century, he and the waitress got to know each other pretty well. One day, when Robert was settling his tab, he asked the waitress if she’d be interested in splitting a lottery ticket with him instead of receiving a tip. She agreed and helped him choose the numbers. Robert called her a few days later to let her know he just won $6 million and that half of that was hers.
Unlike the movie version, the two were both married to other people, and Robert’s wife was more than happy to split the money with Phyllis—but let’s be honest, without the two falling in love, it wouldn’t have been much of a movie.
8. The $184,700 Tip
History repeated itself in 1995, when John Steele, an auto parts worker in Toronto, left a lottery ticket as a tip for his favorite waitress, Tracy Dalton. He asked her to let him know if she won anything and she agreed to share any prizes from the ticket. A few days later, the ticket ended up being worth $184,700, meaning both parties got a cool $92,350.
9. The $70 Lucky Number
While skeptical Redditors point out that this could easily be the customer copy of this receipt and not the legitimate merchant copy, the story behind this image is pretty wonderful if it is true. Supposedly, the customer asked the server to pick a number between one and 10 and when the server picked seven, this was the tip he got.
This post originally appeared in 2013.