Happy Trails! 34 Great Pop Culture Cowboys and Cowgals

In honor of the finale of ''Toughest Cowboy,'' we tip our ten-gallon hats to our tobacco-chewin', guns-blazin', boot-scootin', cattle-drivin' favorites, including John Wayne, Roy Rogers, and Clint Eastwood

By Amy Wilkinson Updated July 26, 2008 at 09:00 PM EDT

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6. Brokeback Mountain (2005)

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Ang Lee's awe-inspiring Western masterpiece follows Ennis Del Mar (Heath Ledger), a tight-mouthed tough guy who falls in love with his fellow cowpoke Jack Twist (Jake Gyllenhaal) but is unable — or, rather, unwilling — to take the relationship past the occasional tryst. Two years since its release, there's no denying that the whole hoopla over Brokeback and its frank sexuality overshadowed a poignant part of its narrative being: proof that cowboys most certainly do cry.

KLEENEX MOMENT His lifelong love dead, crestfallen Ennis clings for dear life to Jack's tattered old shirt.