There is something timeless and endearing about a classic American pickup. The owners/drivers don't speed like a black Audi or cut you off accidentally like a Prius -- and the simple sight of these always puts a smile on my face. I don't have an old round fender pickup in my garage, but if I did, it'd look like this 1953 Ford F-250 Pickup offered for $7,500 in Naples, FL via craigslist. Tip from Dascpcu.
Production of the 3rd generation F-Series started in 1957 and only lasted a few years before it was phased out in 1961. It was a much more modern truck than its predecessor and featured fenders integrated into the body. Find this 1959 Ford F100 offered for $8,400 in Bonita Springs, FL via craigslist. 
Find this 1979 Ford F-250 Wild Thing here on eBay bidding for $5,000 located in Lapeer, MI with 4 days to go.
The sixth generation Ford F-series (1972-1979) featured new boxy-styled sheet metal that wasn't much different from the car it replaced, aside from the items required for safety -- but one of the biggest changes was the extensive use of galvanized thick sheet metal, which is why you see scores of these still driving on the road today. Find this 1976 Ford F-250 Highboy Ranger here on eBay bidding for $6,101 USD ($8,133 CAD...why is this on Canadian eBay??) with 5 days to go, located in Canyon, CA. Tip from Rémi.
The Ford F-series pickup was in its seventh generation for the North American market when they introduced a diesel engine in the 1983 -- largely as a response to the success of GM's diesel which was gaining steam since its introduction in 1978. The early diesel engines were unsophisticated and gutless, and it was only with the introduction of turbocharging that they became comparable and eventually better than their gasoline counterparts. Find this 1986 Ford F250 7.3 TurboDiesel offered for $8,000 in Phoenix, AZ via craigslist.
Take a look at this 1997 Ford F-250 Extended Cab here on eBay bidding for $10,699 reserve-not-met with auction ending on Saturday.
One last quick feature before I take the kids out trick-and-treating, and this is one I wouldn't mind finding in my candy bucket. The sixth generation Ford F-series was produced from 1973 through 1979 on a chassis that was first released in 1965. It was during this generation that the F-series took the prize as the best-selling truck in America, a title it has maintained ever since. Find this 1975 Ford F-250 here on eBay
bidding for $23,000 reserve-not-met with a few hours to go, located in West Jordan, UT.