Once as common as garden gnomes in American suburbs, the grand Cherokee reclaims relevance with a chiseled body, a wood-and-leather-swaddled cabin, and pleasing road manners. A ZF 8-speed transmission, shared with the likes of Bentley, maximizes grunt from a quartet of engines, from frugal gas and diesel V-6s to a 470-horsepower hemi V-8 in the high-performance, charmingly sociopathic SRT8. [$29,790; jeep.com]
Mad Men's Charming Rogue
The man who played Roger Sterling, is moving on – surfing in Montauk, hanging with his son, and directing a feature film.
Plus: Greenpeace's High-Seas Avenger
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