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Shep loved to travel and often spoke about cars and driving down the Jersey Turnpike,  being out in his plane, or driving around New York on his motorcycle.

Note the photos, unless otherwise noted are symbolic of vehicles he owned and are not the actual ones.
 


Cars
 

Shep's Cars as mentioned on various shows.
Thanks to Rich B. for the info

6/6/63  Shep's Beard; Grinding Valves
learned to drive on '37 Pontiac; 1st car a '33 Ford Roadster, black

4/3/65  Great Generator Hunt
'37 Ford

2/25/66  Tell the Story Already
got new blue Ford after the Army

11/16/69  Clunker of All Time
another 1st car, light gray Ford

12/31/76 ?date Mill Mail Truck
GMC/Chevy panel truck, BLUE (says GREEN 12/31/68 ?date

12/31/76 ?date   Pickle Color Paint Job
'49 Ford

3/23/65  NAB Convention
Peugeot 403

12/16/71  Used Cars
Hudson Hornet

3/30/77  Historyland
incident in a Crosley, though not his

7/29/66  Style
'31 Chevy Roadster Independence Cabriolet
 

A photo of Shep's 1931 Chevrolet Independence taken by Fred McDarrah, who also took the famous 'poster shot' and it appeared in one of McDarrah's books, "Beatgeneration".

According to this add in theSpring 1959 issue of the Evergreen Review Shep owned the Gogomobile pictured.
Rover 2000tc was a constant sponsor during the 60's and Shep mentioned that he was expecting delivery on one during one of his shows.
These 2 photos are from author Eugene Bergmann.

The MG-TD.  Several times Shep said he owned one.  In fact, on the October 1971 show called "Devils, Blackout in the Woods" - Shep talks about driving his to Upper Michigan for a fishing trip, then, in the AM, being spooked by the darkness during the day, driving back home.  He says he did this after he got out of the army, before getting a job.  However, that would have been 1944-1945, and the MG-TD was only produced from 1949-1953, so he must have had the TD during or after that period.  I don't know what color his was. 
 
An earlier model of the MG (MG-TC) was produced during 1945-1949, but Shep very specifically said he'd had a TD model, and though they might look similar to a novice, we MG-T series nuts easily tell the difference, and so Shep, a car nut, would not have made such a mistake.  In fact, as the TC is the more classic, more rugged model, he'd have been sure to say TC if that's what he'd owned (In my tape of Shep talking to S.J. Perelman, Perelman says he owned a TC.)

The Morgan (British -he advertised them in the late 1950s/early 1960s)  and actually owned one. When he advertised it on the air he said one could send for a Morgan brochure--and this black and white image is from the very brochure Gene sent for and still has! 


Motorcycles

According to one of the members of the Red Onion Jazz Band, which performed in "Look Charlie", Shep rode a "Cushman" You can see Shep on his Cushman on the first page of the "Look Charlie" program which Shel Silverstein drew. He is riding up the lower leg of the letter "K"


Planes

Shep owned a 1973 Grumman American AA-1A Yankee - FAA # N73JS and it is still registered under his name with the FAA

It was registered April 5, 1973

In the late 60s he took flying lessons at Princeton Airport. His instructor was Bob Hall


Bicycle

Shep claims to have owned a green Elgin bicycle as a kid. It was stolen when he went to the local A&P for bread and left it unattended out front.


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