These are not your average “we met at Comicon, I asked for an autograph” type celebrity encounters. These are up-close and personal, salacious celebrity drive-bys.
This piece is based on an AskReddit thread. Link on the last page.
1. When I was about 13, my cousin surprised me and took me to Leonardo DiCaprios house. My cousins newlywed husband was very good friends with him. This was around 15 years ago too, when Leo was in his absolute prime, and unbeknownst to him I was completely and utterly obsessed.
I’ll never forget sitting on his white leather couch just waiting for him to walk into the room we were all in. Then, all of a sudden, he appeared out of nowhere with a trail of smoke behind him, high as a kite with a fat joint in between his fingers. I didn’t even recognize him due to his scruffy beard and long matted hair.
2. I hung out with Kevin Smith for over an hour Nashville, TN last summer. He was very stoned.
Also, Kevin Smith is the nicest person I’ve ever met, and that’s not just because he was high as a kite.
3. I rode in a hotel elevator with Red Sox pitcherDerek Lowe at like 2 in the morning while he was making out with two women atthe same time.
4. Friend of ours is a hotel hospitality manager. Shewas alone in a room with Russell Brand. He very politely offered to have sexwith her. She said her husband was waiting downstairs for her. Brand said hecould come up too.
5. I was in the bathroom of arestaurant in Vegas taking a crap. In walks someone and sits in the next stall.After a couple moments I hear “holy god what died over there?” Iapologize and eventually get up and wash my hands. As I was drying them theother stall flushes and out steps Ryan Reynolds.
If I hadn’t of just pooped I would’ve pooped in my pants. He looks at me and just shakes his head and asks what I ate so that he doesn’t do this to his wife. I just mutter Subway. But that was not the end of our encounter. (continued…)
Anyways, we continued talking whilehe was drying his hands & he asked where my table was, I tell him, and bythe fate of god he was sitting just a few over. Next thing I know my girlfriendand I are sitting at the same table as Reynolds and his wife.
Honestly the bestthree hour dinner I’ve ever had. I’ve meet other famous people before, but I’venever meet anyone as genuine and down to earth as him.
6. My mom was on herhoneymoon in Hawaii when she bumped into OJ Simpson (before he went crazy).
He looked at herand asked if she wanted to head to his room.
She pointed at herring finger and said “oh I just got married ” He take her hand andputs it down, looks at her and says “that matters why?”
In the end shecalled over my dad and he took a picture of her with OJ Which is now forever inher honeymoon album.
7. Back in the 90’s, when Jean Claude Van Damme wasthe man, my dad was at a Vegas hotel and went down to use the sauna. He was inthere shooting the breeze with a business partner and in walks Van Damme. Hesays “if you are who I think you are, you are my sons favorite actionstar.” Van Damme confirmed and told him to tell me hello from him.
The weird part is that they were all naked.
8. I was shooting behind the scenes photos of a D-list celebrity boxing tournament in college. Washed up celebrity central.
After a long day of witnessing the power of egos and 15 minutess of fame – the Octomom giving me Advil for my back, Coolio calling me a G, and seeing Jose Canseco put on fake tattoo sleeves – I was ready for drink.
But I could never have guessed who I would end up having a drink with. (continued…)
I had been talking to an absolutely beautiful ring girl and she wanted to join me for a beer after the fights ended. We went upstairs to the bar and she went to get us a table. I went over to the bar and while waiting for the drinks, the pornstar Ron Jeremy came up next to me!
He said he had seen me talking to the girl all night and offered to wing-man for me. Luckily my confidence was already sky high for getting the girl to come drink with me, so I politely declined and went to join her waiting at a table nearby.
9. I was at a hotel in SouthAfrica looking for the bathroom when I got lost and ran into LaurenceFishburne in a hallway. I pretended like I didn’t know who he was and asked ifhe knew where the bathroom was, like I probably would have asked anyone anyway.
He was a very nice guy and walked me to the bathroom where he said,”the men’s room is on the left, the women’s room is on the right, thechoice is yours.” I almost died.
10. I had a friend who met Jason Segel at a bar in LA.She said he was fairly drunk and all over the place with their conversation. Atpoint he just point blank said to her, “So are we gonna have sex?”
She said,”No….” He responded “OK” and then just walked away backto his table.
11. Me and my Dad met Rick Astley. I shook his hand, andsaid, “Big fan.”
Dad didn’t shakehis hand: “Sorry, my hands are sticky.”
Rick smiles andsays, “my hands are usually sticky too”, then grins.
12. My sister ran into Matthew McConaughey in a bar years ago. They hit it off, and they went back to her place.
She got overwhelmed by nerves and said she had to go run out to her car to get something. She sat in her car freaking out for god knows how long until he eventually gave up and left. Must’ve baffled the poor guy.
13. My friend was peeing next to Shaq at a club in Miami. Of course he can’t keep his eyes on the road, and tried to sneak a peek at Shaqs junk. Shaq turns to him, smiles and says, “crazy right? Big guy, regular penis.”
14. I got drunk with Christopher Mintz-Plasse (McLovin) once. We would be mid conversation and some new random girl would walk up, he’d stop talking, make out with her for like 2 minutes, and then send them on their way and return to the conversation. Super surreal.
15. I was working on a behind the scenes featurette for a movie starring Keanu Reeves and Renne Zellweger. I had to wire the mic under Renee’s shirt and clip it to her bra, and I totally accidentally grabbed her boob.
She looked me right in the eye and said, Jeez, buy me a drink first okay? Sadly, that did not happen.
16. One of my favorite movies growing up was Crocodile Dundee. Much later in life I am hanging out with a girl I was casually seeing at a hotel bar in San Diego, and Paul Hogan was there.
We put down a few drinks then I figured I would go say whats up and tell him how I loved Crocodile Dundee and see if I could get an autograph.
I was drunk but I remember the interaction pretty clearly – I went over to chat and he was not that cool, which was fine. But then he started asking about the girl I was with and if she would like an autograph. I got the sense he wanted to give her something else as well. (continued)
That lead to him propositioning me for what I thought would be a threesome. I was entertaining this idea, as the thought of tag teaming this girl (who I was not officialy dating) with Mick Dundee would be pretty cool.
So she came over and everything was really cool. Fast-forward 10 mins and he said, why don’t we go up to my room? That “we” didn’t include me. I got to sit at the bar while my friend with benefits went and had sex with Mick Dundee, and he never even gave me that autograph or came back down.
17. I was in a very large men’s room at a performance venue taking a pee. I was about 15 urinals deep and the bathroom was completely empty besides me. In walks Jack Black.
He sidles right up to the urinal next to me. Nothing wierd happened, but I always found it bizzare that he didn’t space himself out better. That’s a man code violation.
18. My friend pantsed (full pantsing with penis out and the whole shabang) his brother and James Franco saw everything.
It was near where John Lennon was shot, by that patch of flowers. His brother was wearing a James Franco selfie t-shirt at the time.
Franco pointed at his shirt and did like a finger gun and wink thing. Then his brother said, “James Franco just winked at me” and then he got pantsed. Franco’s eyes bulged a bit and he started laughing and shaking his head. He never broke pace, just kept walking. After he was a ways past us he loudly said, rockin shirt man!
19. I live in Las Vegas. This happened one summer while I was in high school in the mid 90’s. I had just got my drivers license. I was at the Forum Shops at Caesar’s Palace with a friend and there was a crowd outside the Versace store so we went over to see what was going on.
Mike Tyson and his entourage were shopping inside and they had locked the doors for him. But we wanted to meet Iron Mike! And boy, did we ever. (continued…)
After a while, his entourage disappeared into the back of the store and we realized that they were headed to employee parking behind the store. We ran down the corridor next to the store and headed toward where his crew were loading up Persian rugs and shopping bags into a Range Rover while Iron Mike was putting on a helmet and jumping onto a sport bike.
My buddy and I start waving at him and right as he makes eye contact my friend switches from a wave to flipping him off. Mike ripped off the helmet and started shouting obscenities at us while we ran back into the mall crapping our pants, hoping to God Mike Tyson didnt come kick our asses.
20. My mom grew up with Rob Lowe as her neighbor. She “dated” him in middle school and they were apparently found making out in a closet at school one time. She says that he was one of those kissers that uses enough tongue to lick your vocal cords. Thanks for the heads up, mom.
21. David Spade is exactly the kind of person you’d expect him to be. He opened for Bobcat Goldthwait once, and my roommate’s best friend was Bobcats brother.
I got to go backstage after the show and we were sitting in a circle with Bob’s brother and there was another group of people just standing off to the side.
Bob came out of the shower and sat down next to me and started talking. Genuinely a good guy. Spent 20 minutes talking with him. One of the people standing off to the side was a girl on crutches. I felt bad so I suggested that they pull up a chair and join us. To help her I got up and pulled a chair over for her. I turned around and Spade took my seat, flipped me the bird and told me to f off.
22. I went to Miley Cyrus’ 18th birthday.
Was hanging out with a few friends for a car show in LA and apparently this chick that was with us was dating Miley’s brother. Turns out they were going to Miley’s place for a party and asked us to drop them off. We dropped them off and as we were driving away we decided to hit up the chick to see if she could get us in. She said sure and we ended up partying there for a couple hours.
Hadn’t seen Miley all night and next thing I know I’m in the kitchen and I look over and she’s by the sink taking a hit off a pipe. (continued…)
At that time she was still this perfect Christian Disney star so it was weird seeing her smoking weed just a few feet from me.
Apparently some guys nobody knew ended up sneaking into the party and grabbing a couple purses, to include Miley’s, and ran off. Once that happened they kicked everyone out and we went home.
I found out later that her phone was in the purse and had a video of her smoking salvia, which got released to the public and was the first of many things that changed everyone’s image of her.
23. Chuck Berry got me in a hotel room and told me what he planned to do with me. This was back in the 80’s and I was stupid and naive as hell.
Let’s just say I got the hell out of there.
24. Went to the U2 concert in LA a couple years back and saw Pierce Brosnan walking through the parking lot of the Forum. As I walked by I said: Bond, James Bond. He gave me the most revolting look and said bloody wanker.
Totally made my day.
25. I was at a Jim Jeffries stand up show in Dallas. Sure enough he pounds over 10 beers doing his routine.
After the show he’s hanging at the bar belligerently drunk. My friend and I head over to say what’s up. Before We could say anything, Jim grabs my friend, forcefully bends him over and pretends to bang him from behind in front of everyone there.
Best night of my friends life.
26. Andy Dick tried to pull me into a bathroom after we did some drugs together at a party in Hollywood Hills.
I pulled away but he took my best friend instead.
He never told me what exactly happened.
27. I went to a pool party in LA around 2002 and there was a guy named Michael Buble there.
I don’t think anyone had heard of him at the time. I remember meeting him only because my friend made fun of him when he introduced himself by calling him “Michael Googly Moogly,” which was a reference to a line in a Snickers commercial.
For the rest of the night he was known as “Googly Moogly.” Later that night, I walked into the bathroom in the guesthouse and he was taking a shit. I think it was about a year or two later that he became a big deal.
28. Im a man. I slept with an NFL player six times in three weeks in the late 1990s. He’s never come out; so, I can’t out him, but he’s got a wife and more than a couple children. He’s retired now, but he still does lots of stuff in the public eye: foundations, charities, that sort of shit. I wish him well.
29. This is actually from a director I worked with. In the 80s, he was hired as a backstage dresser for a Broadway show that had Patti LuPone in it and it was his first show.
I don’t remember what the show was, but there was a scene where she runs off stage.
He was instructed to stand right off stage and hold his hands out at a very specific position, which is common in quick change situations where an actor might have to hand off or literally throw a costume piece to make their change.
What actually happened is that his hands were in the perfect position to get two handfulls of boob. As she ran off stage she pulled her breasts out so that he would grab them. Apparently she likes pranking new crew members.
30. Billie Joe Armstrong (Green Day) told Tre Cool (their drummer) to have sex with me. Instead he gave me some orange soda. I’m straight, it worked out.
31. I worked my way through college as a waiter in a gourmet room in Las Vegas. I became acquainted with Florence Henderson (RIP), and she would ask to sit in my station. One evening she had a guest, Joan Rivers. Me. Henderson had a favorite wine, Piesporter, that she always ordered. It just so happened that on our wine list, that wine was labeled as #69.
That’s how she ordered it, I’ll have a bottle of 69. On this night, I approached the table, introduced myself to Ms. Rivers and made the usual small talk, then I asked, “so Ms. Hendetson, would you like a little 69 tonight?” OMG, Joan Rivers went completely insane!
She started screaming and yelling and demanding Security to have me fired and arrested, and the whole time, Florence Henderson is trying to calm her down and explain. Long story short, the Maitre d’ put me in another area and not long after I graduated and left that job, and I never forgot that story This happened in ~ 1985.
32. I asked Winona Ryder out to lunch on an elevator. She said she had to work. I always tell myself “She didn’t say no.
33. Met Gary Busey at an airport in Tulsa, OK. Through a strange course of conversation in which he insulted nearly everyone, he ended with a joke:
Gary: “Did you every hear about the poor family?”
Gary: “They were so poor, they had to j*rk off the dog to feed the cat.”
He then chuckled to himself, grabbed the next taxi, and left us speechless.
34. I was next to the Table of Leo DiCaprio at Catch in NY. Saw him get with an 18-year-old model then proceeded to take her home. Saw them leave together like it was nothing. The girl had the biggest smile on her face too.
35. A guy walked by me at the airport as I sat waiting to board and, I kid you not, farted mere inches from my face. I looked up, it was Bon Jovi.