Hillary Clinton flew my plane nearly every day during her NY Senate campaign, so I got to know her and her staff pretty well. She always made sure to leave the beer and extra meals behind for us, along with the "presidential M&Ms".
I met Bill Clinton twice when he was flying one of our planes someplace and didn't want to attract attention by flying in on one of the 747s. He remembered my name the second time and asked how my family was doing.
Al Gore was the bane of my existence. Literally got kicked in the ass by him one time because I was trying to get something fixed in the cabin and they let him on the plane for some reason. Dude had a real southern plantation owner mentality with anyone he didn't consider an equal or could help him out.
Louis Freeh, who was the Director of the FBI at the time, was so jazzed after flying on my plane that he shook my hand after coming down the ladder and wanted his picture taken with me. Dude had mad energy. A fucking dynamo.
Colin Powell and I traded dad jokes for about 20 minutes once.
Bob Dole was a cranky old bastard. One time, he boarded the aircraft, looked around and said, "Can I get one of the newer ones?" We proceeded to tow a G-IV out of the hangar and prep it for flight, since a G-III wasn't good enough for a failed presidential candidate.
I drove around the guys from Blues Traveler when they were at our base for a USO tour. They were cool. I was voluntold into doing it, and when I showed up to collect them, I went off a bit to smoke a cigarette while their shit was getting loaded into the van. One of them came over to bum one off of me, and was making small talk when he asked, "So is this what you do all the time?"
I told him I got plucked out of roll call that morning and told to report at MWR to pick-up the van to take some fucking band around. He asked, "Do you know who we are?" I nodded, took a drag from the cigarette and exhaled, "Not a fan." We both laughed and everyone got along famously the rest of their time there.
I once pissed-off Madeleine Albright by mistake. I was working the maintenance control center and got a call from some yahoo who dispensed with any pleasantries and said, "The Secretary would like a cake made and ready for when she arrives that reads, 'To [some asshole I don't remember] From the Late, Great, Mouth of State."
I thought it was prank call by someone in the maintenance squadron, so I said, "Well, I'd like to be anywhere but here at 0200, so the Secretary can suck my dick." And I hung up.
A couple of minutes later, the Command Post phone 10 feet away from me rings, and the Captain who answers it does a quick series of, "Yes, yes, of course, my apologies, I don't know, yes, oh yes of course, right away."
She hangs up the phone, turns to me and asks, "Did you tell the Secretary of State to suck your dick?"
"No ma'am, I told some dumbass that the Secretary could suck my dick."
"Well, she just called herself and chewed my ass out. She wants your name and everything. And now I've got to find some place that can bake a cake in two hours."
I told her I thought it was a prank call and had no idea the "Secretary" was the actual Secretary of State, and then said if they ask again that it was SSgt Matt Braxton.
"Who the hell is Matt Braxton?"
"I don't know it's just the name I use when I make reservations or I'm in trouble."
There's a few more that I'm forgetting, but those are the ones that stand out.