Read These Crazy True Stories of the Most Generous Tips Left For Servers

For those who have ever worked in the service industry, you recognize that the worst types of people who inhabit this earth aren’t slow walkers or mouth breathers or even loud chewers. No, you know that the most miserable humans are undoubtedly those who leave pathetic tips at restaurants.

These wretched individuals always have some sort of excuse as why their tips are so dismal, but usually the real reason is simple: they’re assholes.

However, horror stories of bad tippers often get counteracted with anecdotes of benevolent, kind-hearted patrons who recognize serving is no walk in the park. For every incubus who tips $2.00 for a $500 dollar meal, there is a gentle soul who shells out thousands of dollars for an otherwise cheap dinner that helps me believe in humanity again.

$100 Lemonade Stand

The only thing potentially more polarizing than this past Presidential election is the Kardashian/Jenner clan. However, I know at least a few youngins’ who are undeniably Team K. This summer, the youngest Jenner sister, Kylie, was cruising around Los Angeles with her longtime bestie, Anastasia "Stassie" Karanikolaou, in tow when they happened upon a lemonade stand. In true Kylie fashion, the then 18 year old starlet documented the whole escapade of her pulling up to the stand and purchasing a glass of lemonade via Snapchat. She’s seen giving the proprietors of the lemonade stand a crisp $100 bill for their product and offering a “We love you!” before driving off into Kardashian wonderland.


$6,100 To Pay For Tuition

In January of 2014, Abigail Sailor was an archetypical young college student struggling to pay her tuition. A freshman at North Dakota's Trinity College, Sailor worked at a Cracker Barrel to support herself through school. One day, two customers walked into the restaurant and asked to be served by the grumpiest waiter to see if they could make him or her smile. When told they didn’t have any grumpy servers, the pair were seated in Sailor’s section as she was deemed the happiest waitress. When prompted, Sailor told the pair about her rough upbringing from losing her mother at a young age, to growing up in foster care and being abused by her foster father. Evidently touched by her story, one of the guests, who also happened to be a Trinity Alum, wrote her two checks: one a $5,000 tuition check and the other a $1,000 check for supplies. He also left a $100 tip for good measure, which Sailor gleefully split with a coworker.

$10,000 Pizza Hut Tip

Though admittedly I haven’t been to a Pizza Hut in quite a while, I’m fairly certain the pies don’t inherently warrant a $10,000 tip. For Jessica Osborne, however, this was the case when a family of regulars gifted her the life changing tip. In 2007, Osborne was 20 years old and a recent college dropout due to financial struggles thwarting her from continuing her education. She shared this with a regular patron named Becky, who also had been going through a tough time having recently lost her husband and eldest daughter in a car accident. After hearing Osborne's story, Becky thought it’d be the “right thing to do” to use money garnered from the accident’s large settlement and help Jessica finish school by granting her $10,000.


$47,000 From Paris Hilton

It’s no secret the notorious heiress of the Hilton fortune is stupid rich, so to speak, but sometimes we just need a little reminder. In September of 2014, the eldest Hilton sister did what she does best (no I don’t mean DJing) and went out to a ~trendy~ Nightclub in New York City called Marquee. Joined by a slew of her fellow one percenters, the table ended up with a bar tab of $230,000 after ordering giant bottles of Ace of Spades Champagne, and 11 bottles each of Patrón, Cristal, and Grey Goose. Having been raised right, Paris left about a 20% tip which ended up equating to $47,000. Though I’m sure working that table was no easy feat, it’s likely worth it for a tip that could buy you a brand new Audi.

$20,000 From A Benevolent Millionaire

Melissa Mainer distinctly remembers that Benjamin Olewine’s bill was only $3.45. However, that didn’t stop the 92 year old do-gooder from tipping Mainer almost 5,800 times that amount. On track to become a registered nurse in April of 2014, Mainer was working at the Peachtree restaurant in Harrisburg Pennsylvania. 92 year old Olewine was a regular patron as well as Chairman Emeritus at Sysco Central Pennsylvania, a food distribution company. Working to pay off her massive nursing school debt, Olewine took the opportunity to share his wealth and pay off all her tuition bills amounting to about $20,000. Mainer is currently a debt free registered nurse thanks to her kind hearted benefactor.


$4,000 Tip Courtesy Of Johnny Depp

There’s a lot to talk about when it comes to Johnny Depp–his knee quivering good looks, his dramatic relationship with Amber Heard, or how he may or may not be the man behind the Brangelina split (Google It). Yet, whatever you want to say about the 53 year old A-lister, one thing you can’t say is that he’s not generous. When filming Public Enemies, Depp frequented Gibson’s Steakhouse where he was often served by one Mohammed A. Sekhani. After a night of poppin’ bottles totalling around $500 worth of wine, the Pirates Of The Caribbean star tipped Sekhani $4000. He was obviously elated and said of Depp, “I have waited on 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… He may be one of the most famous actors in the world, but he is a very humble guy and a really cool dude.”

$3 Million Winning Lottery Ticket

A classic for a reason, the tale that inspired the 1994 film It Could Happen To You is one of the most iconic anecdotes of tipping gone right. Robert Cunningham, who’s portrayed by Nicholas Cage in the movie adaption of this story, was a long time regular at Sal’s Pizzeria in New York. He had a favorite waitress at the restaurant named Phyllis Penzo who had been working there for over two decades. One day, in lieu of a tip, Cunningham offered Penzo a deal to split a lottery ticket he had in his pocket. She accepted and they chose the numbers together for Cunningham's $1 entry in the New York State Lotto Competition. Ironically, on April Fools Day Cunningham discovered the ticket was worth $6 Million dollars. The two, as promised, split the money evenly amounting to a payout of $285,715 a year over 21 years.