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


We published a piece a while back in which people discussed the experiences they had as high school classmates of those who went on to become millionaires or well-known celebrities. More readers related their own tales of their now-famous or wealthy classmates in the comments section. The following are a few of the most intriguing ones:
Notice: There is no verification for these tales. It is alleged that the users are speaking from personal experience.

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.”

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.”

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.”

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.”

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.”

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.”

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.”

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.”

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.”

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.'”

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

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.”

“I’m very thrilled for him and his continued success; he was always a genuinely kind guy, as I mentioned before. It’s truly amazing to watch individuals thrive once they leave high school.”

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!”

As one might anticipate from a basketball star, he was also extraordinarily tall, making it simple to locate him in the corridor because he stood out above the others. With a multimillion-dollar contract, the Celtics player seems to still be playing at an extremely high level.”

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.”\

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.”

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.”

“As usual, before our late-night musical session, I asked her if she would like to grab a bite to eat. I brought her back a bag so she wouldn’t be hungry because her guards wouldn’t allow her leave. I once bought dinner for a millionaire at that same moment.

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 — PsychCold CaseMonkGotham, etc. If you watch Young Sheldon, he’s the guy who tried to get George fired last season.”

“He played football, did musicals, and was lovely. Watching a TV show and then all of a sudden, he appears on television is kind of funny.”

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!”

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.”

“His early entrance into a well-known band did not surprise anyone. He continues to communicate with my brother.”

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.”

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.”

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

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.”

“After making investments in other properties, my ‘brother’ was left with the property.” I am fighting to retire, yet he is a multimillionaire. But he’s remained the same ‘brother’ from our childhood, unchanged over the years.”

Apartment for rent

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Aria Skylark


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