I've met my share of "famous" libertarian types, but it's the wife that has met/spoken with a ton of legitimately famous peeps. Vince Vaughn, Peter Billingsly (You'll shoot your eye out!), Jesse Ventura, William Shatner (I got an autographed photo out of that one lol), Owen or Luke Wilson (I don't remember which is which) etc. She was there when Sacha Baron Cohen punked her boss for
Bruno and recognized him immediately when he made the mistake of poking his head around a corner; otherwise they would have had no idea what just went down. She went on a bunch of cable news shows with people like Bill O'Reilly, Tucker Carlson, James Carville, etc. but those were remote so she didn't meet any of them in person. She still friendly with Tucker Carlson, though.
We've been to several parties at the Playboy Mansion, and met some famous people, but the only ones I remember off the top of my head were Kendra (former Hef girlfriend) and Adam Carolla.
I've met Andrew Napolitano, John Stossel, Barry Goldwater Jr., Ron and Rand Paul (duh), etc. The wife and I have been out on Ron Paul's speedboat with Ron, Tom Woods and his wife, and Barry Goldwater Jr. Drinking in the hotal pool with Barry AuH2O Jr. was entertaining. Adam Kokesh is a friend of ours; in fact he stayed with us for a couple of days recently when he moved to WDC to start his new show on RT (Adam vs. The Man, 7pm est on Russia Today). Rob Kampia (Marijuana Policy Project) is a friend; last year we watched 4th of July fireworks from his rooftop hot tub. I guess he's not so much famous outside of libertarian/marijuana advocacy circles.
My grandfather was in a jazz band with the infamous
Oliver Naquin when they were at the Naval Academy together. My great great uncle of some sort was
Charles Dewitt Brower, "King of the Arctic." You can read his autobiography
online, too. Highly recommended. He had some crazy adventures. I have a bunch more family stories because my aunt is into genealogy.
I own a classical guitar that my aunt (same one) gave me that was played once by Andres Segovia.