A little bit of everything. I liked some of them very much, and some I absolutely hated.
The big shots, the real ones like Sam Zell and Flip Filipowski, treated me like an equal (conversationally anyway.) I'd spend an hour or two driving guys like that around, and they'd talk my ear off. First name basis. Handshake at the end of the charter. Great memories of those rides.
The assholes were the posers. "Yes driver, we'll be making a stop at A&W. We'd like root-beer floats." They book a $30 shared ride to the airport, and they act like I'm Jeeves their personal driver.
At first it was mainly airport work. 10-12 trips a day. Half outbound, half inbound. Tedious, and (as you know) tough on the body, tough on the sleep cycle, tough on the digestive tract. That's where I encountered the majority of the shitheads.
Towards the end, the last year and a half or so, it was mainly charters with maybe 20-30 regular customers. Very little airport work (except for Frank's wife Elise. Good god that woman travelled. 6 pc set of Louis Vuitton luggage for a 3 day trip.)
Texans? We both hate Texans?
One of my unforgettable Texas fares was a mother and her 5 kids. Pick up at the Omni in the Loop going to Midway. They'd been on Oprah. (Harpo Studios was a fucking massive account. 5-10 cars every weekday) Anyway, I get this lady and her kids loaded up, and hit the Outer Drive going south. She starts telling me about her wonderful stay in Chicago, and the wonderful people at Harpo, and goes on to tell me that they were on the show to discuss the fact that she doesn't allow her children to watch any television. "Ahhh won't evin lit theyum watch the rerun of the Oprah Show with theyum on it!"...."That's very interesting.".......couple of minutes later, she sticks her face through the partition opening and asks...."Excuse me, but is that Lake Chicago?"......"Uh, no ma'am. That's Lake Michigan. It's one of the Great Lakes."....."Ahhh see." (maybe turn on a TV once in awhile.)
Ski area Texans. Oh man did I hate those people. Friggin' cowboy hats and matching ski outfits. I'll never forget the time I was in a lift line at Snowmass. Asked my (then) mother-in-law what's with the droplets on the brim of that guy's cowboy hat. (in front of us in line) Before the mom-in-law has a chance to answer, Mrs. Texas turns around and gives me the death stare...."Don't you know innnythang? It means he's an awl-man."....Mother-in-law starts snickering and says..."That means oil. They're probably from Texas." Mrs. Texas glares at her......Move forward they're next up....annnnnd Mr. Awl Man looks over his outside shoulder to line up with the approaching chair (dumbass), misses by half-a-butt-cheek, gets knocked on his ass, and his fancy Stetson gets knocked in the snow. That was sweet.