If there’s one thing we all like to do, it’s complain about celebrities. Sometimes, we complain about their behavior; sometimes, we complain about their money; sometimes, we complain about their horrible sense of fashion (and the awful trends they set); or sometimes, we just complain about their fame. One thing that people definitely love to do is complain about the tipping habits of the stars. Hollywood (and Broadway, for that matter) is always rife with gossip about which reality starlet didn’t leave a tip, or which NFL superstar left $5 on a $500 lobster meal. It happens all of the time. I mean, there’s a reason why NBA legend Scottie Pippen, a Hall of Famer, six-time champion, and second fiddle to Michael Jordan (a man who earned almost $110 million in his career) was referred to as “No-Tipping Pippen” during his time in Chicago because he was a truly terrible tipper and no one ever let him forget it — that’s what happens when you’re a celeb.
But, fortunately for us all, and for the news services and entertainment magazines that love human interest and uplifting stories just as much as they love dirt, there are also plenty of celebs out there who are great tippers. I’m not talking great tippers in the way you and I might be, leaving a 25% tip on a $100 check at the local steakhouse because we had a really fun even out. No, I’m talking about the way people with real bank can roll when they want to, flashing wads of cash for pizza delivery boys, baristas, and bartenders. Read on to see who in the entertainment world has been a great tipper in the past and just exactly what they gave.
15. Charlize Theron – $100 for a $4 Smoothie
Sometimes, a celebrity becomes known for being a good tipper even if they didn’t necessarily intend to be one. Now, I’m not saying Charlize Theron isn’t a good tipper in general; I’ve never heard any stories that make me think she’s an evil person or anything like that. But check out this story, and you can decide whether she would have done the same if she had her money with her originally. It seems that Charlize had a hankering for a frozen smoothie or something recently, so she popped into a Pinkberry (a place I myself have never popped into and probably never will) in Hollywood and grabbed a $4 cup of frozen goodness. The only problem was that Charlize didn’t have any cash. She promised to be right back if the counter person let her go with her treat, and the employee did. Charlize did come back about 30 minutes later — with a $100 bill in hand for the employee. Now that’s thanking someone!
14. Bill Murray – The Coolest Guy in Hollywood
I suppose it’s no surprise that Bill Murray would be a great tipper. After all, he appears to be one of the coolest guys to ever hit Hollywood. He also appears to be one of the most down-to-earth dudes who have never forgotten what it’s like to toil in obscurity. If you don’t believe me, you should check out the video of Murray hanging out at a Chicago house party last fall while his beloved Cubs made their incredible run to the World Series championship (yeah, that’s fellow Superfan Eddie Vedder there also). So anyway, what does a regular guy who makes it big do when he’s out on the town? He tips big, if not outrageously. He recently left about a $75 tip on a $60 bill at a local bar. The best part is that Murray is known for doing stuff like this all the time, not just once.
13. Taylor Swift – $500 Tip Plus Concert Tickets for a Meal
On the other hand, it came as a great surprise to me that T-Swift would be such an awesome tipper. Who knew? She completely seems like the type who, if given bad or even mediocre service, would rip the waiter or waitress publicly and maybe even write a song about what a jerk they were to her. Alright, I exaggerate, but “America’s Sweetheart” has developed a reputation as being somewhat of a ‘B,’ so you just never know. It turns out, though, that Tay Tay can be a real queen when she wants to. After a meal at a Philadelphia restaurant a few years back, she left a $500 tip. $500 is a very decent chunk of change. Not only that, but when she found out that the chef’s kid was a huge fan of hers, she gave him two tickets to her concert in town. Wow — that sounds like something Bill Murray would do!
12. Brad Pitt – $800 for Sushi…in Berlin
It just doesn’t seem like a surprise to hear that Brad Pitt is a good tipper. Notice I didn’t say anything about his old flame Angelina Jolie — she seems like the type who might stick you with the butter knife if you didn’t provide perfect service. OK, I jest. But Brad, for all of his well-documented marital issues over the years, really does seem like a plainspoken, normal, genuinely friendly star. There have been varied reports as to his generosity as a tipper over the years but none more remarkable than one from just a few years ago. It seems Brad and Angie really enjoyed a Japanese sushi meal they had in Berlin (yes — sushi in Berlin; we live in a small world these days). In fact, Brad was so pleased, he left an $800 tip and thanked the staff for their service. No word has come out on whether Angie approved.
11. Ellen DeGeneres – Tipped The Pizza Guy $1000 At The 2014 Oscars
Ellen sure seems like someone who enjoys giving a good tip. Am I right or am I right? After all, everyone knows how generous she can be on her hit daytime TV show The Ellen DeGeneres Show. Not only did she come up with the Christmas-themed “Twelve Days of Giveaways,” where everyone in her audience gets tons of really pricey freebies, but she even expanded that initiative to a spring giveaway as well. So sure, we all know Ellen is pretty cool. But how cool is she for real, I ask you? Well, apparently, she is all that all the time, too. A case in point occurred during her bit at the 2014 Oscars when Ellen tipped a pizza delivery guy $1,000 for bringing her and the other stars a few slices. No, I don’t know how many pizzas he actually delivered, but it would have to be like $7,000 to justify a tip that size — that’s hundreds of pizzas. Somehow, I think Ellen’s tip was based on generosity, not quantity… Well, and a bit of publicity, too.
10. David Beckham – 1000 Percent of $100 Equals?
Good old Becks has all the money in the world, all the fame in the world, every major soccer championship that matters, a movie named after him (Bend It Like Beckham) and a hot wife who was once a Spice Girl. So it’s really no wonder that he supposedly enjoys being a good guy when he’s out on the town. Hard work, talent, and a little bit of luck gave him a life many people would envy — why not share? That’s exactly what he did a few seasons ago when he was still playing for the LA Galaxy of MLS. Beckham brought a few teammates into a restaurant called Joxer Daily’s Pub for a few beers and apps. The bill came to $100. I bet you can guess how much of a tip Becks left the astounded waitress. That’s right — he added one more zero to the total for the tip and left an amazing 1,000% tip of… $1,000.
9. Jessica Simpson – Leaves Big Tip, Plus Handwritten Notes.
Jessica has been in the public eye for a long time now and has always been someone that pretty much nobody has any problem making fun of, regardless of how hot she is. However, nobody has ever accused her of being mean or uncool, as far as I know. In fact, Jessica seems pretty nice as a person, something that’s supported by her tipping actions. Way back in 2011, Simpson was dining at New York City’s Lavo restaurant and was obviously moved to excess by her meal. She left a $300 tip. Her check was $500, which means Jess gave her waitress a staggering 60% tip. Not only that — she also left a cool note that said, “You were amazing and make this world a better place. Love, Jess.” Hmm, it’s known that she had a dinner of veal parm, fried Oreos, and Macallan. I wonder if the scotch had anything to do with the tip???
8. Russell Crowe – $800 and a Guitar Solo
This one is probably going to come as a shocker to most of you readers out there. I know it did to me — not because Russell isn’t an awesome actor — he’s been in a ton of seminal movies like L.A. Confidential, A Beautiful Mind, Gladiator (for which he won a Best Actor Oscar), and The Insider (for which he should have won a Best Actor Oscar), to name just a few. The man has serious talent. He also seems to have a serious knack for getting into trouble publicly, especially with the paparazzi. Perhaps that’s the key right there — he gets into trouble when he’s hounded. When he’s left alone except for good service, as apparently happened at The Carew Inn in Wales in 2009 while he was filming Robin Hood, Russell can be quite a charmer. Not only did the superstar leave a tip of nearly $800 to his servers there, but he also pulled out a guitar and sang for the wait staff. Now that’s service with a smile.
7. Amy Schumer – $1000 on a $77 Bill
Her tips might not be the absolute largest on this list, but there’s a reason Amy Schumer is pretty high up this list: because she keeps on giving great tips. It’s not a one-time deal with her. Some celebrities never forget their roots, which makes it easier for them to remember the little guy. Back when she was a struggling New York City actress, Amy bartended and waited tables to make ends meet, so she knows firsthand what the life is all about. Maybe that’s why she once left an $80 tip on a tiny bill with a handwritten note that said, “I’ve been there; I get it. You guys are great.” Not only that, but just last year, while attending everyone’s favorite musical Hamilton, she left a $1,000 tip for the bartenders working the lobby during intermission. That’s right — $1,000. Her total bill you ask? $77. Now that’s classy.
6. Dr. Dre – Shocker of the Year
Some guys work hard to make their bones and never seem to forget their own origin story, rewarding the “little guy” later in their lives. Three years ago, thanks to his massive Beats by Dr. Dre empire and his success as a producer, the infamous Dr. Dre became a billionaire, joining the ranks of some very exclusive celebrities indeed. For perspective, Taylor Swift and Adele combined don’t make one billionaire — at least not yet. So what do you do when you become a billionaire? Well, in June 2014, Dre first bought Tom Brady and Gisele Bundchen’s old mansion for $40 million. Then, I assume, to celebrate his new status, the hip-hop mogul went out to party at the Hollywood watering hole Skybar. He must have had himself a damn good evening because at the end of it, rather than dropping the mic, he dropped a $5,000 tip on the unsuspecting wait staff. Now that, my friends, is what’s called in his business as fronting!
5. Johnny Depp – $4000 for Wine!
Everyone knows that Johnny Depp is one of the coolest celebrities out there (well, everyone except for Amber Heard, it turns out). I mean, the guy makes both monster franchise hit movies and cool offbeat ones, he plays in a band called “Hollywood Vampires” with Joe Perry and Alice Cooper, and he has all of the coolest tattoos money can buy. Apparently, money can buy some other things, too — things like absolute notoriety for being an awesome tipper. It seems that Johnny has long been known to be an excellent tipper, but one incident in Chicago takes the cake (or wine, as the case may be). Johnny was there filming the movie Public Enemies and spent many an evening at the Chicago steakhouse institution Gibson’s. On one of his last nights there, he and friends consumed a ton of $500 bottles of wine and left in a good mood. He left his server in an even better mood since he tipped the lucky guy $4,000! Yup, that’s three zeroes.
4. Charles Barkley – $25K for Blackjack Dealer
If there’s one thing you can count on with Charles Barkley, it’s that he’s not shy at all about speaking his mind whether you agree with him or not. So we have this next tipping story on good authority — Sir Charles himself. In 2014, during an appearance on The Conan O’Brien Show, Charles told Conan that he thought it was important for stars and celebs to tip well. Basically, he said, if you’re in that position, use it for good. To prove his point, he brought up a $25,000 tip he once left to a blackjack dealer after he had won $700,000. The best part of his story, however, is that Charles felt a little bit guilty about not tipping more. I’m not sure he needs to though. In fact, I’m pretty sure that blackjack dealer would let him shoot at his table again any old time. Nothing but net, Charles — nothing but net!
3. Paris Hilton – $47K Tip at Nightclub
Here’s another celebrity whom everyone likes to gang up on, whether it be for her awful sex tape, her terrible reality show excesses, her weird choice of “career” as a DJ, or her actual excesses of wealth. If you’ve ever seen the pictures of the dog house she “built” her $13,000 Pomeranian, then you know just how wasteful and decadent Paris seems to the real world. But get this: in 2014, Paris decided to party with some friends at New York City nightclub Marquee. And oh, what a party it was, as they bought $100,000 worth of champagne (Cristal, mostly) and spent almost another $100,000 on many, many bottles of Grey Goose and Patron. I’m assuming that they shared it out — Grey Goose isn’t that expensive. Anyway, when it came time to pay the bar bill, Paris surprised everyone by putting down a massive $47,000 tip. It seems an evening with Paris might be worth it after all!
2. Jay Z – 50K on $250,000 Bill
Here’s the deal with rappers, producers, DJs, MCs and the whole hip-hop community in general: not only do they usually really like to party, but they also really like their bling, and they really, really like to show how flush with cash they are. It should be zero surprise then to note that Jay Z, who is pretty much the most successful guy in that industry ever, would like to throw his money around. I mean, just check out any one of his videos for proof! In real life, Jay Z was once partying with his crew in a Miami nightclub. When I say “partying,” please remember that the very rich are very different from you and me. Jay Z dropped over $250,000 on champagne at this nightclub. So what do you do when you run up a quarter-of-a-million-dollar bar tab? Well, you tip the bartenders $50,000, of course. Yup, you read that right — $50,000 on a freaking bar tip.
1. Nicolas Cage (Sort Of…)
Alright, alright… maybe I lied just a little bit here. Nic Cage himself wasn’t actually the one delivered the largest tip to a waitress that anyone has ever heard about. All he did was play the guy in the movie based on this real-life story. I mean, I’m willing to bet that there are some crazy tipping stories out there about the man who played Ghost Rider, both good and bad, but this one is just a case of him and Bridget Fonda making a true story more famous than it ever would have been otherwise. What really happened is that Yonkers cop Robert Cunningham, a regular at a joint called South Pizzeria, offered to split any winnings from a lottery ticket with his usual waitress, Phyllis Penzo. Each of them chose three numbers and forgot about it for a few days. That is, until their Pick-Six turned into a $6-million winner. And yes, Bob did the right thing without even thinking about it, splitting the ticket with Phyllis. She walked away with a $3 million tip, the largest in history.
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