9 Of The Luckiest Tips Ever Received By Waiters

Waiting tables is likely the most unrewarding job in the world; the only redemption being tips. By law, employers are not obligated to pay servers even minimum wage because tips are expected to over compensate. On top of being underpaid, the majority of hospitality workers are spoken down to, constantly having to deal with disrespectful customers. In very rare instances though, every once in a while, a customer will come along, who more than makes up for all of the unpleasant interactions, tipping far beyond the expected percentage and even changing a restaurant staffer's life. Here are 9 of the luckiest tips ever received by a waiter.

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9 Kristen Ruggiero - $458


Single mother of three, Kristen Ruggiero thought it was a mistake when a couple who spent $42 on dinner left behind $500 to settle their bill. The waitress assumed the pair had intended to leave five $10 bills, instead of the $100 bills that she'd found, so she decided to set the change aside until the regulars returned to the restaurant, where upon she handed the change money back. The couple assured Kristen that they had intended for her to keep the change, insisting she deserved it for the exceptional service they received. Kristen gratefully excepted and used the extra money to pay off some bills, as well as treat her children to a trip to Six Flags.

8 Mohammed A Sekhani - $4,000


Mohammed A. Sekhani was tipped $4,000 by actor Johnny Depp, who became a regular at Gibson's Steakhouse while filming Public Enemies. After an evening of bottle after bottle of $500 wines, the a-lister graciously tipped Mohammed $4000 for his services who had this to say about Johnny: "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 — when I wait for him he doesn't like to be too fussed over and is not in any way demanding. He may be one of the most famous actors in the world, but he is a very humble guy and a really cool dude."

7 7.Greg Rubar - $5,000

A couple who were long time regulars at D'amico's Italian Market Cafe gifted their favorite waiter, Greg Rubar fifty $100 bills ($5000) as a tip after finding out that the young man lost his car in a flood a few weeks earlier. Greg who had been serving at the restaurant for 16 years, and regularly waiting on the couple for 8 years, was reluctant to accept such a large sum but they refused to take it back, insisting he use the money to replace his hold car, and assuring him that although they would remain regulars, they wouldn't be tipping him for a while. The couples meal total was only $27.

6 Abigail Sailors - $6,100

Abigail Sailors, a freshman working her way through Trinity College, received a $6000 tip from first time customers of a Nebraska Cracker Barrel. Initially, the pair walked into the restaurant asking to be served by the grumpiest waiter, with the intention of making their day, but were instead sat with the pleasant Abigail Sailors, who shared touching information about her tough upbringing in foster care and her financial struggles to pay for school. The two patrons were moved enough by her story to write two checks: 1 for $5000 and another for $1000. The checks were topped off with a $100 bill, half of which Abigail split with a fellow waiter.

5 Jessica Osbourne - $10,000


Pizza Hut waitress, Jessica Osbourne received a $10,000 tip one evening from a regular patron named Becky, who would come in for a pie every Friday. While serving Becky, Jessica shared that she recently had to drop out of college due to financial struggles that prevented her from being able to pay her tuition. Becky had also been experiencing tough times, tragically losing her husband and daughter in an automobile accident, and sympathized with Jessica by giving her $10,000 out of a large settlement she'd received. The waitress was astounded, exclaiming that of all restaurants, she works at a Pizza Hut, and that just doesn't happen there everyday.

4 Melissa Mainer- $20,000


92-year old Millionaire, Benjamin Olewine who is a regular at a Pennsylvania Peachtree Restaurant, tipped Nursing student Melissa Mainer, an astounding $20,000 to pay for her nursing school tuition. According to the waitress, the senior citizen's bill only amounted to $3.45, and she was in shock when he offered to cover all of her tuition fees, after sharing a bit of her background with him. Today, Melissa is a debt free registered nurse. Benjamin, who is Chairman Emeritus at Syscos Central Pennsylvania, says he would be happy to pay for Melissa's grad school education as well.

3 Paris Hilton leaves $47,000 tip


Perhaps the most generous known tip ever gifted by a celebrity was recently given by none other than socialite Paris Hilton, who tipped an unheard amount of $47,000 on her $230,000 bill at Marquee Nightclub. It's unclear exactly who the recipient of the tip was but needless to say, they were easily the luckiest bartender working that night.

2 Tracy Dalton - $92,350


In 1995, instead of tipping his favorite waitress Tracy Dalton, John Steele left her a lottery ticket with the only contingency being to let him know if she won anything, which she agreed to do. To her shock and amazement, the ticket turned out to be worth $184,700 which the waitress happily split in half with the regular patron.

1 Phyllis Penzo - $3 million


The 1994 movie, It Could Happen To You, featuring Nicolas Cage and Rosie Perez is loosely based on this very story. Robert Cunningham was a long time regular at Sal's Pizzeria, where his favorite waitress, Phyllis Penzo worked for over 2 decades. In place of a tip, Robert offered the waitress the chance to split a lottery ticket for which they both picked the numbers. A few days later, Robert discovered the ticket was worth $6 million and true to his word, phoned Phyllis to let her know $3 million of it was hers. The payout was $285,715 a year for 21 years.

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