Content edited for clarity. The moments that a person is in a taxi, limo, uber, etc can be so many things. Most of the time it's quiet and a bit awkward unless you get a chatty driver. For these chauffeurs, these drives were anything but. All of their secrets are out now and we can see just how weird being the driver can get.
"Billy Bob Thornton was doing radio press for a movie about to come out, meaning he had to stop by six or seven radio stations for interviews. He wanted to have a cig in the vehicle on the way to the next interview but I had to let him know our company has a no smoking policy in our vehicles.
He asked me to call the owner to make an exception but the owner said no and it was a $250 cleaning fee if he smoked in the vehicle.
He asked to stop by a bank, Came out and handed me $5,000 cash, and said, 'Here's for the whole Goddam pack"
He smoked in the car the rest of the trip. Later I got up the nerve to ask him if that's the most expensive pack of cigs he had ever smoked? All he said was, 'Not even close,' and never explained it further.
He tipped me on top of the $5k and was extremely generous. The owner let me keep half of the $5k, so overall it was a pretty great day."
"I picked up a wedding party: bride, bridesmaid, and bride’s boyfriend who was paying for the wedding. They had a magnum of bubbly and we drove around for quite some time while they snorted coke in the back. They were using rolled-up $50s and $20s, then tossing them to me in the front seat as tip money. I dutifully brushed off each bill and added them to my wallet, pretending not to know what was going on.
The 'couple' argued off and on about showing up to the wedding, apparently, she felt weird about getting married and he was trying to convince her it was a good idea. Finally dropped them off at the church and he slipped me a matchbook with his name and number written on it. Scored a sweet leather jacket with the tips from that night.
But there was the groom, waiting dutifully at the church. The boyfriend was paying for the bride’s wedding to the groom. That was an eye-opener for me, too.
I never found out what happened between any of them. Once I dropped them off, it was on to another weird saga. Never called the number in the matchbook either: I recognized my naïveté and that world was way beyond me. So this was the late 80s and limos were still pretty newish for the general public. We treated them as private spaces although I found out later they are considered public spaces. I was 19. It was exciting (and probably stupid) but I felt no fear. I thought I could handle anything. I think I was just really freakin’ lucky. I thought that if I wasn’t doing the coke/drinking, then I was safe. I can’t imagine doing that myself in a limo, as a passenger, but I don’t do anything like that either so I don’t know. "
"When we were in high school, my friend used to caddy at a local country club. One guy really liked him and asked if he would be willing to drive him around while he went out partying (this was like 2003 and in a pretty rural area), my friend agreed.
He picked the guy up at like 8:00 pm. Right off the bat, the guy handed him $200. He went to a bar for a little bit, my friend sat in the car. The guy came out, handed him another $200, and told him he had to visit his friend real quick. He went and got a bunch of coke. They went to another bar, he handed my friend another hundred dollars and told him to look out the window and turn up the radio (he then blew several lines).
He came out a couple of hours later with a girl (he was married with kids). He handed my friend another $200 and they went back to her house. After they did the hanky panky, he came out and asked to be taken to the beach.
At this point, it was like 2:00-3:00 am. My friend said that the guy slowly walked around the beach, went into the water up to his ankles (in his shoes), threw a bunch of rocks into the water, and then sat in the sand for about 45 minutes.
He came back to the car and asked to be driven home. When they got out of the car he hugged my friend and gave him $500 and asked him to never tell anyone what happened.
None of us really believed my friend when this happened until the guy he drove got arrested for assault and possession of coke like six months later."
"Friend of mine worked for an upscale concierge chauffeur service. His most memorable moment came when he lost Marie Osmond. Fairly simple gig, 'go to the airport and pick up Marie Osmond,' who was to be the featured entertainer at a private event. The plane came in, he met her, she had a carry-on bag but her checked suitcase, containing her stage dresses and makeup, was missing.
She was unflappable, though, and asked to be taken to the nearest upscale mall. He did as instructed, she went into a large upscale department store, selected two long sequined dresses, and went to the fitting room to try them on (without him, of course).
Unfortunately, there were two entrances and exits to the fitting room, and Marie Osmond exited out through the other side and could not find my chauffeur buddy, who was waiting patiently on the side she'd entered. About 20 minutes passed. He thought something had gone wrong, so he grabbed a female manager and asked her to go into the fitting rooms and ask for Marie Osmond. The manager thought she was being pranked and declined.
Chauffeur buddy was in mini-panic mode now, running wildly around the store asking random customers, 'Have you seen Marie Osmond? Have you seen Marie Osmond?'
The store security was summoned and he was asked to leave the premises right then. He called his employer and told them he had lost Marie Osmond. The employer didn't have her cell phone number but had her agent's number and he was not accepting calls.
She had in the meantime taken a cab to the gig, thinking she had been forgotten. Lots of apologies eventually ensued and there were no repercussions."
"I drove L.I.M.O. at Marquette University during undergrad and grad school. Some of the students that went there were obscenely wealthy. Limos are the vans that drive wasted students anywhere on campus and a few blocks outside of campus. Couple of things I remember randomly from it:
It is a free service and a frat star tried to pay me for the ride with a ziplock baggie of coke. I said no, and he called me a legend and left a $20 in the cupholder before I realized it.
Rich kids are rich but foreign rich kids are usually on a different level. Was talking to a guy from Spain who said his dad did something with movies over there. He had an actual Rolex on and ended the conversation with, 'So anyways, do you know where to find any crank?'
Mardi Gras is the name of a campus ministry trip where you use your spring break to build houses and drink in somewhere that doesn't get snow in April. One of the people on my van was getting a free night of drinks from his buddies because he paid for everyone's trips. I think it was like $1,500 per person.
I picked up a couple of girls from a sorority and they spent the entire ride talking about how it was ridiculous that one of the girls' parents planned on making her pay for her own apartment after graduation and there was nothing even livable under $2K a month. The school is in Milwaukee, Wisconsin.
This wasted guy left his wallet on a van and another driver called it in so another supervisor and I can take it to campus police. We picked up the wallet from the driver and opened it to get the student ID so they would know who to email. There had to be a few grand in there. When we called the kid to tell him about it he told us we could just keep it because it was too far from his dorm to bother picking up."
"A buddy of mine ended up driving a Netflix producer while doing Uber. He said they had a great conversation as he brought him to his hotel. The producer invited him up for a drink and since my friend was a film student he thought it'd be a good idea to go and try to get some good networking in. They hung out for about an hour when he asked my friend if he knew of any massage places with 'happy endings.' He didn't, but the guy paid him $500 to bring him to the closest massage place which was only a few miles out. Upon dropping him off he gave my buddy a card and said, 'There's a big party/festival I'm hosting. That's your ticket in. I'll let you know then if I get that happy ending haha!'
He got the happy ending"
"I used to drive limousine and taxi. One time, I got the manager of a fairly famous Canadian band in my car asking me 'where' to buy coke. I had no idea where and I told him that, so his bright idea was to find a girl, hire her and ask her. I told him I couldn't help him pick up girls either. He was disappointed but understood. He had me drive down a well-known street until he saw one. He asked me to pull over, got out of the taxi, paid the fare, and then immediately flagged me down again as a 'new ride.' I knew what was up, but whatever. He got back into the car with the girl and she told him exactly what house to go to for some coke. I took them there and wait a bit, they came back out and I drove him back to the venue.
Then he offers me two free tickets to the show which I gladly accepted as I love that band and had seen them three times. Alas, since I was still working during the show, I gave them away to two friends who had never seen the band. They had a good time and I had a fun story to share with them about how I scored those tickets.."
"About 25 years ago, I had a summer job at a very tony country club. There was a six-figure joining fee, five-figure continuing membership dues, and that got you nothing but the privilege of paying top dollar for rounds, food, etc. I was a porter some of the time, as we had cottages on club grounds for members to stay and make a weekend of it. One of my duties was driving members to and from airports - usually private airports for private jets.
One time, I was driving two guys to the airport and one of them started complaining. Seems he and his wife were always fighting over who gets the jet every weekend, and where they want to go. Well, the other one replied that his third jet was actually just gathering dust right now since his son went to college. He asked, 'Wanna take it off my hands?'
They shook on it right there in the van."
"A small part of my family was Chicago Mafia.
Grandpa told me a story of a family wedding in Chicago they went to in the late '60s. They were picked up at the airport by a limo with some high-ranking family members. On the way to the hotel, they were stopped about eight times by various police officers. The officer would walk up to the driver's window. The chauffeur would reach into a money bag and pass a bill to the officer. Nothing would be said and they'd take off again.
Eventually, my grandpa asked if they were being bribed. His cousin (mafia) laughed and said, 'No it's Thursday. That's when we pay our boys.'
So I guess that's how they did it. Looked like a traffic stop and in the open where it's not unexpected. So I'd imagine that chauffer had seen some things."
"I did drive Uber black for a while in NYC. Had a few interesting situations.
One time I was driving a young woman and right before the destination she screamed for me to pull over. When I asked her what was wrong, she pointed to the couple that was kissing in front of the building. Apparently, the man was her fiancé. She didn't get out, she didn't cry, but she did ask if I could take her back to where I picked her up. I'll never forget her face, it was the saddest face I have ever seen in person.
Another time I was picking up a group of guys outside a club early in the morning, and as the first guy stumbled in, a Glock fell out of his coat pocket. We just locked eyes and I said, 'Hope that's not for me haha.' I was nervous and didn't really know what to do/say.
Probably my favorite was picking up two college-aged girls from what I can only assume was a party. They were very wasted, and the second girl was basically completely gone. They were going all the way to Ridgewood, which was almost an hour. Girl A was pretty talkative and funny, girl B looked to be completely passed out/sleeping and didn't move the whole trip. We made it to Ridgewood, and Girl B sits up suddenly, looks around, opens the door, and vomits EVERYWHERE. She seemed fine after that, but I just kept thanking her for making it the whole way and not throwing up all over my car."
"Not all of them were rich, but a few were Rich, but I drove my boss' friends around so they could meet up and swing.
Sometimes, they'd rent out space by a local lake and sometimes it'd be at a normal upper-middle-class looking home. Other times it'd be a home with floor-to-ceiling glass windows 30 feet in the air and formed a triangle at the top giant residential mansions. Most of the driving around was to either pick up people, drop people off, getting KY items, or cans of red stripe. One time, I ordered 100 taquitos from Whataburger the morning after.
I would be buying things at adult shops for these people and they would prefer to be picked up and dropped off alone or with their plus one. Carpooling was a big no-no. Nobody wore robes, but I did see some people had those Masquerade Ball masks. People were friendly and talkative before being dropped off. Normally slept on the ride home.
Few occasions that stuck out was a guy who had taken that little blue pill for the first time and told me all about it and another guy who took his contacts out beforehand and always asked to borrow my contact solution and case.
If you hadn't known they were swingers you'd think they were just hiring a designated driver to keep people from getting drinking while driving charges. Especially because none of them were particularly attractive, at least to me."
"I drove a 180' Super Stretch Cadillac Fleetwood Brougham in the mid-’90s. There was this elderly Japanese gentleman who would fly into our city several times a month, on his own Gulf Stream no less. I believe he was an early video game developer. Always dressed to the nines, tons of bling, a different Patek Phillippe watch every time. He always traveled with a young male intern, usually the same one for a few trips, then a new one the next month.
He would get in the car, exchange a few pleasantries and then close the divider for the 45 drive into the city. Even with the divider closed, I could usually still hear muffled conversation. One time I thought I heard different sounds though and I noted the whole car, despite weighing about eight tons was rocking side to side.
The first thing that came to my mind, naive me back then, was that the old man had a heart attack and the young man was doing CPR. I lowered the divider to see if he was OK. Well, he wasn’t having a heart attack and they both had happy looks on their faces. I said, 'Hey, are you guys, oh, forget it.'
I put the divider back up and kept driving, wondering how many shots it was going to take to wash that mental image out of my Cerebral Cortex. I estimated a lot and I was right! When we got to the hotel they both acted as nothing happened. Although I noted the intern was walking a bit funny."
"I drove the Chancellor for a large University around and was told to actively forget everything I heard in the car. Throughout my undergrad career, I constantly heard about massive cuts to the Humanities and Fine Arts budgets because we simply didn’t have the money. Multiple building's worth of people were forced to share a single, outdated building during five-year-long renovations. Graduate students and University staff were criminally underpaid and underfunded. RAs were missing out on their salaries when the campus closed despite protections in their contracts. All in the name of budget shortages.
I overheard the Chancellor and the head of the Athletics department discussing an enormous, multimillion-dollar training facility that was being commissioned on land that we were buying off-campus. Our current training facilities are fairly new and our sports teams do not draw any crowds. We also bought an entire campus over a hundred miles away. This place and the administration were awful."
"I drove a few celebrity athletes to signings and stuff but the craziest things were what the quiet billionaires who had $10M summer homes in my area would talk about. Nothing depraved or dangerous. Quite the opposite, really. The mundanity of life with a security that few can fathom.
One guy, I would pick up in Manhattan twice a week and drive him home to his summer house. Gigantic. I live in a four-bed, two-and-a-half-bath with a finished basement. It would fit in his pool house. One drive he's laughing with his business partner about a phone call he had on speaker. A major retailer was trying to back out of a deal because the merch was not making it on time. He talked around it, sending them news articles about slow shipping due to emergency tariffs and War on Terror blockades. It was like someone trying to sell you the extended warranty but he kept the deal. The next week, he's was freaking out bricks because we're stuck in traffic with nowhere to go and he's going to be late to a fundraiser his wife started for his kid's school. He made a big box store fold like a cheap suit but 'unhappy wife, unhappy life.'
Another was an older lady who was the community gossip. She was going on and on, telling the stories of these prominent families who all belonged to the same house of worship. One was pretty well known and influential but, as she would tell it, flat broke. The rest of their community could not let it seem that way and buoyed them up. They kept living in mansions and driving high-end imports and getting added to business deals as a tertiary partner to replenish the fortune like rain gathering in a bucket.
One of my favorites was a guy who probably wasn't a billionaire but he was in the nine-figure range easy. He always had great cars and tipped well but explained that all his cars were bought off-lease. Someone else paid too much to drive it for two years and now he paid for a top-end car but for a reasonable price. Any time he wasn't headed to his office or to get smashed at his country club, he was in jeans and a polo or a concert T-shirt. When his father-in-law died, a nice old man that we often drove to medical appointments, he texted each of the drivers from the service to thank us for driving him and having conversations with him as he always had a good time and brought our stories back with him (most of us active or retired military or LEOs.)
People who could buy a country if they wanted but really just people in the end."
"I met a limo driver in Atlanta with some of the best stories. He was a driver for years and had driven politicians, rappers, lottery winners, dealers, the whole gambit of the human condition that would call for him for a ride.
The company I work for had a contract with the company he worked for so he would drive me to the office once every six months for like three years.
Here are some of the highlights he told me.
There was this one old rich lady. She hired the company to drive her to New York. The catch was she wanted to detour through Knoxville so she could stop at every single Cracker Barrel along the route. She chose the route with the most Cracker Barrels. To quote him, 'It's Cracker Barrel they are all the same. She wanted to stop at Every. Single. One.' The trip was supposed to take two days and ended up taking four because of Cracker Barrel.
There was one guy who must have either won the lottery or been a thief. He didn't know why this guy had money but he got a call to a bad neighborhood. He was nervous driving a limo in the slums of Atlanta. He picks the guy up and he is struggling with this wad of cash. The guy asks the limo driver if he knows where he can get some coke. To quote the limo driver again, 'I'm a limo driver, of course, I know where to get coke.'
So he went to the spot grabbed this guy an eight-ball and gave it to him. The guy asked the driver if he knew where he could get a girl. Again to quote the driver, 'I'm a limo driver, of course, I know where to get some girls.'
So the guy has a pile of coke and a blonde chick in the back of the limo. The driver says it's strange because this guy is swinging way outside his weight class. The girl acted like it was Christmas and was hogging the coke. So the guy finally got the bag away from her and dumped it on the table in the back. He was about to rail a line when the girl popped the sunroof on the freeway. The wind blew the dust around the inside of the limo like a tornado. At this point in the story, the driver was cracking up and said, 'The girl was frantic and tried to snort the dust out of the carpet. Ah hahaha'. I was cracking up he was cracking up. I thought he was going to crash just telling me the story.
He said the guy asked him to get him some more but he had to call someone else to his hotel because in his words, 'You don't buy an eight-ball and then show up an hour later for another without questions.'
There was also this politician. This driver got a job for a woman. They drove around a bunch of mostly business-type buildings, corporate type of stuff. His company did a lot of business with corporate headquarters and staff. She finished and asked him to go to one last place where they pick up some random guy. He dropped them off at a hotel and left. He picked them up the next day and took them to the airport.
Fast forward to the next week and the company called him asking what happened. He was confused. They said a lot of reporters and people were asking questions about what happened with his passenger. He didn't know what was happening. Then the company got contacted by the FBI and some investigators.
At this point, he was spooked and bails. He stayed home to avoid work. His friend at the company gave him the number of an agent that wanted to question him. He went to a phone outside his neighborhood and called the agent. The agent asked him about every stop and every person the lady he drove stopped or met. They got descriptions and then let him go.
Turns out the guy was a married politician banging a corporate executive. A huge scandal ensued."