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Keith Hart

Keith Hart

Portland, OR


1958 Cadillac Fleetwood 60 Special
Portland, OR
per day
I always knew that I wanted either a 2-seat roadster or something with giant tailfins.

Several years ago I decided to follow a crazy dream and become a part-time Elvis impersonator. This choice led me town a crazy path but also finally set an official direction for my vehicle search.

Elvis LOVED his Cadillacs! Some say he bought over 200 and gave most away.

While Elvis drove more than 20 different models over the years, the pink 1955 Fleetwood Sixty Special is the most iconic.

Of course everyone wants the 1959, and why not? Those tailfins and bullet taillights are spectacular!

But Elvis never actually owned a 1959. He did own a 1958 Cadillac limousine. The story goes that after buying Graceland, Elvis took his 1957 limousine to get some chickens, ducks, peacocks, and a turkey. Even after sending the car to the dealer to be cleaned, it was never the same again. That car was then traded in for a 1958 version.

That was all it took and my search began.

I searched and searched for the perfect 1958. I knew I wanted the Fleetwood Sixty Special and it had to be black. I came across one that looked perfect, but by the time I contacted the seller it was already being held for a transport to take it to Finland.

I found another beautiful one, this time out of Houston, but they were asking too much money and I had to pass on it.

I kept searching and researching.

Then, a few years ago, this beautiful lady shows up in one of my searches. As I started digging into the photos I realized that this was the exact same car I saw a few years earlier from Houston, this time she was being sold out of New Jersey and the price was within my range.

After a lot of research, and sending a mobile inspector to check out the car, I sent my money and brought her back across the country.

At her first car show, the 2019 Rose City Round-Up, she took Best of Show. She has also taken a few other awards at some other shows. She was on the cover of Downbeat Drag in June of 2020 and also featured in a photo shoot in Car Kulture Deluxe in May/June 2021.


David Goodspeed
We had an amazing day cruising with Keith in this beautiful machine! Keith was a charming & personable host and his Caddy was comfy and just plain cool. Great memories made, don’t hesitate to reach out to Keith to have a blast!
Jun 18, 2021
Laura Brown
We hired Keith for our Oregon wine country wedding, and could not have been more pleased. The car is a stunner and it was a big hit at the wedding, both for us and our guests! Our pictures with the car are some of my favorite of the whole night. Keith was incredibly gracious, both in our interactions leading up to the wedding and the night of. Absolutely recommend hiring Keith and renting this beautiful car for whatever you may need!
Jun 15, 2022
Michael Bachkanji
Great experience!! Great driver!! Amazing car!! it felt like a dream leaving the wedding in the Caddie! People downtown were breaking their necks to catch a glimpse of us rolling through. Highly recommend Keith!!
Aug 26, 2022
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