23 Funny And Unexpected Stories From People Who Went To School With Celebs And Wealthy People

A while back, we wrote a post where people shared what their high school classmates who went on to become millionaires — or famous celebrities — were like back then. In the comments, more readers shared their own stories of their now-famous or wealthy classmates. Here are some of the most fascinating ones:

Disclaimer: These stories have not been verified. The users are supposedly speaking from their own experiences.

1."I went to high school with Debbi Fields, who later went on to found Mrs. Fields Cookies. Yes, she baked really good cookies even back then. Fields is her married name."


Closeup of Debbi Fields
Ron Galella / Ron Galella Collection via Getty Images

2."I went to school with Adam Sandler from fifth grade through ninth grade (when I moved to Texas from New Hampshire). He was just as goofy then as he is now. Every time I see the French class sketch on SNL with him and Alec Baldwin, I laugh because I just know he based that on our eighth-grade French class and teacher, lol."


Closeup of Adam Sandler
Todd Owyoung / NBC via Getty Images

3."I went to high school with an Olympic figure skating medalist. I didn’t know him (it was a big school, and he was a grade younger), but he had the same French teacher I did, and she absolutely loved him. I also went to high school with Danielle Panabaker for a year. My AP English teacher was also the speech team coach, and she was on the speech team. He gushed about her."


Danielle Panabaker
Joe Scarnici / FilmMagic / Getty Images

4."I went to high school with a guy who was fairly popular and nice. After college, ended up working at the same large corporation. He left after a few years to work for his father’s company and made it grow. He founded his own company and did very well — like, he had a building named after him at the university, one of the largest homes in the city, etc. However, his company got sued after the death of an employee and his wife."

"The company had none of the normal safety protocols that other companies in this industry have as standard. The company was also fined by OSHA (Occupational Safety and Health Administration) — a big deal — and was the subject of an investigation by a national safety board. So, he’s still in business."


A businessman looking at his iPad
Kobus Louw / Getty Images

5."I went to middle school in upstate NY with a New York Times photographer named Hilary Swift. I don’t remember a lot about her to be honest — just that she had perfect attendance in sixth grade and also that I thought she was kinda cute. I came to realize that a lot of the really intelligent, creative, and high-achieving people I knew growing up don’t stick around past high school because there’s really nothing for them to do in a place like that."

"I’m always happy to learn about people like Hilary who got out and made something of themselves because I know from personal experience how easy it is to get stuck there."


A camera
Jan Hakan Dahlstrom / Getty Images

6."The Geico Caveman (John Lehr) was a classmate of mine. Also, Paul Rudd went to my high school, but he was a freshman when I was a senior. Jason Sudeikis graduated a few years later and lived in my neighborhood."


Side-by-side of John Lehr, Paul Rudd, and Jason Sudeikis
Getty Images

7."I went to high school with Khris Middleton. He was a great guy, treated everyone with respect, worked hard on-and-off the court, and was humble and down-to-earth. He deserves everything he's getting in the NBA."


Khris Middleton
Chris Schwegler / NBAE via Getty Images

8."My first serious boyfriend, when I was 14–16, was Mark Stoermer. He is now the bass player for The Killers. I also went to school with the girl group 702. We went to a performing arts high school."


Side-by-side of Mark Stoermer and 702
Getty Images

9."A friend went to high school with Taylor Lautner. She said at the time, he had only been in Sharkboy and Lavagirl, and a lot of people made fun of him for that, and then, when he was in Twilight a couple of years later, the same people were bragging about knowing him."


Taylor Lautner
Jamie Mccarthy / Getty Images

10."I went to high school with a girl who came from a well-known family (their last name is a household word) who later married a very famous musician. In high school, she was friendly, but it was obvious she had goals set way beyond the average person. We did not hang out. We were acquaintances. I just thought she was a bit stuck-up. At the time, I had no idea really who she was or that her family would open those kinds of doors for her. I think she accomplished her goals, becoming wealthy and famous as the wife of 'someone.'"

"I hope she was happy and got what she was hoping for. Life is a journey, and you brush shoulders with all kinds of people as you pass down the road."


A woman holding a glass of champagne on a private plane
Lightfieldstudios / Getty Images / iStockphoto

11."I went to middle and high school with Jessica Simpson's husband, Eric Johnson. He was just a regular kid. Quiet, though."


Jessica Simpson and Eric Johnson
Ella Hovsepian / Getty Images

12."I went to high school with someone who is now a fairly popular emcee for some Hollywood events and TV programs. He was about two years older, but we shared a couple of art elective classes. What really amazed me when he first started was when I saw him on TV, and my jaw hit the floor. He was an extremely shy kid but always extremely nice to everyone — to see him now become a crowd entertainer was watching someone do a complete 180."

"Very happy for him and the success he still continues to have; as I said, he was always a really nice guy. It's really great to see people flourish out of the confinements of high school."


Someone using a movie clapboard
Guruxoox / Getty Images / iStockphoto

13."I went to high school with a guy who now plays basketball for the Boston Celtics! He and his younger brother were both basketball stars, and everyone in school knew them because of that. I didn't know them super well, mostly just in passing, but they carried our school's basketball team while they were there. Both of them were kind of cocky because they knew they were good, but the oldest one was overall sweet, and their dad was super nice!"

"He was also insanely tall, as expected of a basketball player, and it was easy to find him in the hallway because he stuck out over everyone else. The one playing for the Celtics is on a multimillion-dollar contract, and apparently, is still playing super well!"


Boston Celtics court
Joe Murphy / NBAE via Getty Images

14."I went to an American school in Madrid with Natalie Morales (used to be on The Today Show). She was a couple of years older than me, so I didn't know her that well, but she had a reputation as being really sweet and studious."


Natalie Morales
NBCU Photo Bank via Getty Images

15."I was in school with an NFL football player. Huge ego and kind of a jerk all four years. Part of his issue was that his dad and uncle were both pro football players, so he already thought he was hot sh*t in high school."


Kevin Sabitus / Getty Images

16."I also went to school with a girl whose father won the lottery. First lottery ticket he ever bought in his life and won $69 million AFTER taxes. It was wild. They went from lower middle class to multimillionaires overnight. She was my friend, but two years younger. She had to have a bodyguard in school because they started getting death threats."

"I asked her if she wanted to grab a bite before musical rehearsal like I always did when we had late-night rehearsal. Her bodyguard wouldn’t let her go, so I brought her back a bag so she wouldn’t be hungry. That was the time I bought food for a millionaire. 😂"


Someone holding a wad of cash
Monica Murphy / Getty Images

17."I went to school from elementary to high school with an actor named Drew Powell. He's not super famous per se, but he has done a lot of work — Psych, Cold Case, Monk, Gotham, etc. If you watch Young Sheldon, he's the guy who tried to get George fired last season."

"He was nice, did musicals, and played football. It's kind of funny to be watching a TV show, and then randomly, he pops up on screen."


Drew Powell
Amanda Edwards / Getty Images

18."I went to middle school/high school with Rezz (a famous DJ); she was really chill and grounded. I remember her telling a teacher she wanted to try DJ’ing as a career, and the teacher laughed at her. Last year, she was nominated for album of the year. I love that for her!"


Rezz onstage
Zachary Mazur / Getty Images

19."I went to school with a guy who joined the group Kool & the Gang right out of high school. This guy took AP classes with me and was an all-around great guy, despite being an excellent musician and literally jamming with all the major talent that passed through Buffalo, New York. He was cool to everyone and was just liked by everyone. He was super handsome and very humble."

"No one was surprised that he joined a major band so young. He still keeps in touch with my brother."


Kool & the Gang onstage
Ethan Miller / Getty Images

20."I went to HS with Danny Amendola in Texas (he graduated a year before me in '03). And yeah, he was the typical football jock you'd expect. I was part of the yearbook staff, and we had to go around and ask questions, take pictures, etc., and he wasn't exactly the nicest but also not a jerk. Kind of in between."


Closeup of Danny Amendola
Cooper Neill / Getty Images

21."My friend went to high school with Brooke Shields in NJ. They both were cheerleaders. My friend said she was really shy and really nice."


Brooke Shields
Taylor Hill / Getty Images

22."I went to school with someone who went on to play for the Denver Broncos. He was a senior when I was a freshman. He was a super sweet guy. I wasn’t paying attention in the hallway and ran into him once. Literally fully ran into him — it was like hitting a brick wall. I fell down, and he helped me pick up my books and made sure that I was okay and wasn’t hurt before walking away."


Denver Broncos stadium
Icon Sportswire / Icon Sportswire via Getty Images

And finally...

23."My dad’s best friend was an amazing person and bought a property many miles away from a major city when I and his oldest son were just babies. My dad thought he was out of his mind, but some of my best childhood memories were on that property. Fast-forward 50 years, and that property is now part of the expansion of that major city."

"My 'brother' inherited the property after also investing in other properties. He is a millionaire while I am struggling to retire. He hasn’t changed in all these years, however, and is still the 'brother' he was when we were kids."


Apartment for rent
Getty Images

Have you gone to school with someone who later became rich (and/or a celeb)? Tell us about it in the comments below!

Note: Some responses have been edited for length and/or clarity.