1963 Oldsmobile F-85 Cutlass

Because my calendar tells me it's convertible season, I've decided to drive another drop-top into the Lotto Garage. You know, when most people think about compact convertibles from the 1960s thoughts immediately conjure up a Mustang, Camaro, Barracuda… you know, all of the usual suspects. I'm shopping outside the box; and tonight I stumbled upon this white Cutlass, which I think looks great with the black steelies and dog dishes. An aluminum V-8 with a stick shift put out 185 horsepower — plenty for an old fart out for leisurely Sunday drives. And the brochure points out how my butt will be caressed in foam-padded bucket seats finished in — are you ready? — "beautifully tailored rich Morocceen…" Wow! Open roads, here I come! (Let's give the photo credit here to hartogrob over on flickriver.com). — jc

2009 VW GTI

Probably just about my favorite all-around everyday driver of all time, this particular GTI is for sale right now (as of this writing) on eBay, and it pushed all of my buttons: fifth generation model ✔, dark gray ✔, four doors ✔, cool plaid interior ✔… If you've ever driven a GTI you can probably understand my enthusiasm. If you haven't, get thee to the nearest GTI and gettest thyself behind the wheel! — jc