9 Absolutely Amazing Tipping Stories [Updated]

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We hear a lot of bad stories about cheap tippers and even cruel tippers, but it’s a lot rarer to 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 working in a pizzeria and watching his best friend work as a waitress while going to school. 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 last year, 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 to leave $500 tips at restaurants around the country, starting in August of last year. All of the events are documented on Youtube videos that are linked to on Aaron’s memorial website.

Since the website was set up last year, Aaron’s family has already collected $65,000 and given back over $22,000 in tips so far. 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 said. 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 is a single mom of three who has had a tough time making ends meet by working the restaurant job she’s held for the last 15 years. One day last year, 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 five hundreds thinking they were ten dollar bills. So Kristen 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," Kristen said.

Grateful for the tip, Kristen 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 Shea’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 Shea’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 been waiting on one particular couple at the restaurant for eight years when the customers handed him fifty $100 bills. The man told Greg, “I’m not going to be giving you a tip for awhile. Take this money. Go buy yourself a car. ”

The instructions to buy a car weren’t just random—the couple knew that Greg recently lost his car when it was flooded in a thunderstorm a few weeks prior. In fact, the waiter had to take taxies 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 Continues To Be Awesome

Flickr: ATempletonPhoto.com

As if we need another reason to admire Johnny Depp, it turns out that he’s also a fantastic tipper. While filming Public Enemies, the star visited Gibson’s steakhouse 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 wines. When they left, Depp left the serve 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,” said server Mohammed A . Sekhani. “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. Nice Gals Don’t Always Finish Last

Most waiters who received a $12,000 tip wouldn’t report it to the IRS, let alone turn it into the police. But Stacy Knutson is a very honest woman and after customers left her perhaps the most generous tip in history, she turned it into the police, worried it was stolen or tied in with some other 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 thus 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 to the waitress.

7. The World’s Largest 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 Nicholas Cage.

In 1984, Police detective Robert Cunningham was a regular at Sal’s Pizzeria for eight years. As Phyllis Penzo waited tables there six nights a week for 24 years, 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 dollars and that half of that was hers.

Unlike the movie version, the two were both happily 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. It Could Happen to Someone Else Too

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. Pick A 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 1 and 10 and when the server picked 7, this is the tip he got.

UPDATE: The original version of this story included a $10,000 tip by Donald Trump that was too good to be true. We very much regret our error.

May 21, 2013 - 2:00pm
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