1993 GMC Sierra 2500 SLX (6-Lug 3/4 Ton) - Bought it from my Dad's work when I was 15, couldn't wait to turn 16. Pro's: Great first truck, went anywhere, loud, paid hardly anything for it. Con's: Motor blew at 53,000 miles.
1999 Chevy Silverado 1500 - LS Extended Cab Z71. Pro's: Real nice truck, all kinds of options that I wasn't used to (Power windows, A/C). Fast and Smooth riding. Con's: High Mileage, Rust, 3-doors, Window Regulators.
2006 Chevy Silverado 1500 - LT1 Extended Cab Z71. Pro's: Very nice truck, basically an upgraded version of my 1999. Everything was great about this truck, only traded it because I got a lot of money for it. Con's: None that I can think of.
2010 GMC Sierra 1500 - SLE2 Extended Cab. Quite the step up in luxury from my 2006. Power bucket seats climate control, all the goodies. Pro's: Everything. Con's: Why can't I turn the cargo light on without the dome light coming on? (But that's seriously it, love this truck)