I don't have any actual pictures of anything he had, but my dad was (and still is) a gearhead. I got my sickness mostly from him and a few family friends who egged me on as well.
When he was younger, he had a few interesting cars:
1960 Ford Fairlane
My dad's had the stinkbug stance and one of those light-up cat 3rd brake lights from a JC Whitney catalog in the back window. Total late 60's high school kid car.
1966 Olds Cutlass Supreme 4 door hardtop:
His was red with a black vinyl top and had Olds SSI wheels with redline tires. It was a sleeper, too! It had a warmed over 330ci High Compression V8 backed by a Hurst shifted Muncie, but had a bench seat, for extra sleepiness. He used to street race the thing locally, and said it was surprisingly quick.
1969 Pontiac Lemans Sport
He later picked up a more tame car after his street racing sleeper days. His Lemans had a 350 H.O. and an automatic, and he only had it for a little while, because he said that it was "terrible in the winter". He liked it, but wishes he got a GTO instead.
After that, he went full Brougham for a while.
1970 Olds 98 Convertible
He got a good job in the early 70's, and wanted a really nice car to share with my mom. They found this Olds (just like the one in the pic), and it was a special order car with every factory option. This was the first car I remember taking a ride in, and the car I went home from the hospital in back in 1982. They got rid of it in 1987, and I was there when the tow truck came and took it away because the engine "seized" from sitting at a body shop after a fender bender. My mom cried. They still want this one back more than all of the others.
He also tried his hand at the "fuel efficient yet kinda sporty 70's Japanese car" game:
1975 Datsun 710:
He wanted to like this one. During the gas crunch in the 70's, he caved in and bought one of these (I think it was blue). He had a lot of problems with it, and later gave it to one of our neighbors whose daughter needed a car. Of course, after she got it, she had zero issues with it and drove it forever. 
He did like it a lot when it was working correctly, though. It was the first Nissan product my family bought, and they later went back and bought a 1996 Maxima and a 2014 Infiniti Q60, both of which they think pretty highly of.
He also liked his sporty trucks:
1983 Ford F150 Flareside:
His looked like the gray striped one, but was not an XLS. His was an XLT! It had running boards, white wagon wheels, cab lights, and similar red stripes and a red interior. His had the 300ci I6 and an automatic. This was the 1st car I remember going to a dealership to buy. He stupidly traded it in on a whim for a 1987 Dodge Dakota, which was a horrendous pile of suck. This was also the vehicle that taught me the term "it broke down", when the fuel pump quit in the middle of a rain storm on the way to my grandmother's house while my mom was driving. I got to walk the rest of the way there. I also learned the acronym Found On Road Dead that day. 
1992 Ford F150 Flareside "Nite":
After he got sick and tired of replacing oil pumps in his 1987 Dodge Dakota (seriously, he went through three!!!) he began pining for that F150 he had, so when he saw this F150 sitting at a dealer up the street around 1994, he snagged it immediately. This one was really cool: 5.0 V8, 4x4, and the rare "Nite" appearance package, which consisted of a blue-to-purple side stripe, cool wheels, and blacked out everything. It did have a few issues (brake problems, ignition modules) but it was a big step up from the Dakota. It also served as my daily driver for a while in college. In the end, the rear leaf spring mounts rotted off, the cab corners were starting to go, and it needed a rear main seal, so he sold it for $500. I sorta wish I hung onto it. One of the best looking trucks ever IMHO, and he loved that thing.
Honorable mention: 1984-85 Ford Escort GT TURBO
This is a fun one. My dad wanted to give another stab to the sporty fuel efficient commuter car thing, so when he saw one of these at the dealer, he bought one new. His was black with orange and red stripes, and had a 5-speed manual. He broke down on the way home from the dealer. The cause? a bad fuel pump. But man, was it a looker! I thought it was the coolest car ever when I was a kid, and loved riding in it. It was the polar opposite of our other car at the time: that big green 1970 Olds 98. He only had it for a few years because it was unreliable. I would love to find one of these, especially with the phone dial wheels! They were rare then and practically nonexistent now.
I've been trying in recent years to get my dad, who is going to be 67 this year, to sell his 2003 Harley FLHTC 100th Anniversary Edition and get an old muscle car era convertible. I think both him and my mom would enjoy it better than riding on the bike, which he barely rides these days.
. He claims to have beaten 289 Cobras and pretty much any 'vette at autocrosses, which were called gymkhanas back in those days.
