I went on a double date in college in Boston ca 1970. The other girl’s date was Jay Leno.
A friend of mine became an actress and stuntwoman. She’s worked on a lot of well-known movies, but primarily behind the scenes and in bit roles – most of what she and her husband (who is somewhat more well-known) do is train actors on how to act like soldiers or warriors.
If you’re willing to go to a degree of separation:
- A high-school classmate of mine married an Olympic figure skater.
- My wife went to high school with a future NBA all-star.
- My sister briefly worked with Jeffrey Dahmer (just a few months before he was arrested).
When my wife was in high school, there was a band that practiced in the garage just down the street from her house. A couple of years later, they finally had a break when one of their songs was used in a movie. It was Survivor. 
Lead dancer at the Lido in Paris.
Movie producer, nothing huge, but he was one of many on Ever After.
Given the quality of my high school and the funds the other kids’ parents had to funnel into their education, I’m sure most of them have been pretty successful. A lot of doctors, lawyers, politicians and business owners. I’m an outlier.
I went to Junior High and High School with Jeremy Jawsinski, who was one of the three guys in the bomb The Real Cancun.
He was a pretty big jerk all though school.
i have none of my own. i was involved in theater throughout middle and high school, and some of my classmates now work as actors/models, but none of them have made it big.
my family has a couple of these, though. my aunt went to high school with elvis. she didn’t like him (she described him as a “greaser”). my mom did theater with michael jeter in college. she also went out with billy joel once. i feel like my dad knows someone or other famous from back in the day but i’m drawing a blank on who. they have all the interesting stories!
A college acquaintance now edits the conservative British political magazine The Spectator. He’s well known in political circles, but not exactly a household name.
I was at school with the guitarist from indie rock band Mogwai, who I guess are also somewhat famous. We’re not exactly best buddies, but we would stop to talk to each other in the street if our paths happened to cross.
I went to school with Cynthia Powell, John Lennon’s first wife. I was at Julian Lennon’s christening which happened to be at the same time as my sisters baby. John didn’t turn up.
I went to High School with someone who is Internet Famous. This person has a popular website and over a million Twitter followers but I imagine they could walk around without that many people recognizing them.
Someone else who was a grade ahead of me went into the NFL and turned a brief career there into some acting.
Similar to this, there is at least one famous person who went to my high school, but I didn’t know them at the time, even though technically I went there at the same time that he did, because my high school was an integrated 2-12 school and he was in elementary school at the time.
Actor Peter MacNicol was in my fourth grade class; in fact he’s standing right behind me in our class picture (and looks exactly the same). We were co-clowns and walked home from school together. He often played the fool but was whip-smart with great comic timing even then.
Not really, I know some semi-famous people, but not that well. My cousin’s band briefly flirted with fame and still makes enough money from it to live on, but they’re really only known in certain circles.
The band Radiohead are “friends of a friend” and I saw them at the friends wedding, but I didn’t directly speak to them, despite the fact the first tape I ever bought was “High and Dry” from their second album.
I was friends with Paul Rudd in elementary school until his family moved away.
I went to school with this guy* for a year in elementary school where we were kind of close, and then all through high school where we were chummy but didn’t run in the same circles. NYC didn’t treat him well and he’s back home where I saw him at the high school reunion and occasionally at the grocery store to say hi.
*sorry I didn’t write his name but I don’t want to set off a Google Alert. Also, you probably don’t know him anyway
I’d tell you, but then I’d have to kill you.
Whoa! What did she say he was like?
Not exactly a friend, but an acquaintance of mine from high school is a current NFL starting quarterback.
My mother went to high school with Paul Krugman.
I once had a roommate whose mother had dated Ted Kaczynski in high school.
Crispin Glover was a good friend of mine in our teen years. We lost touch a very long time ago but he would certainly know who I am.
In college I lived in the same dorm as Christopher Reeve for two years.
A friend of mine from high school became a TV actor. In one of his roles he got whacked by Tony Soprano.
Not someone I went to school with, but I dated someone for a while who later became a Space Shuttle astronaut.