Picking a favorite scene from The Sandlot is no easy task. Do I go with the s'mores lecture or the epic tobacco barf scene? What about Benny's P.F. Flyer powered mad dash from The Beast? All great, but I've got to go with the one that made Michael 'Squints' Palledorous (Chauncey Leopardi) my favorite sandlot ballplayer, his desperate attempt to snag a kiss from the pool's hottest lifeguard, Wendy Peffercorn (Marley Shelton).
What happens when it's so hot Ham is "baking like a toasted cheeser?" The boys make like a "can't hack it panty waist who wears their mama's bra" and ditch the baseball diamond for a dip in the local pool. But escape from the relentless heat isn't the only reason the group goes for a swim, it's because the lifeguard is Wendy Peffercorn. The whole group is mesmerized by her "lotioning, oiling, oiling, lotioning," but it's Squints who gets pushed to the brink.
He's a young kid to begin with, but Squints is particularly small for his age and when that bony little boy sporting Speedo shorts and a pair of thick black glasses waltzes up to the diving board, we get a taste of exactly what's about to go down. He creeps up to the edge, takes off his specs and brings the buildup to the max giving Wendy a quick wave before plunging into the deep end. In a matter of seconds his buds freak, Wendy dives in for the rescue and Squints is back on dry land in the perfect position, laying on the ground, looking like a dead fish while Wendy gives him mouth-to-mouth.
And then it happens; Squints shoots a grin in his genuinely concerned friends' direction and when Wendy least expects it, "This Magic Moment" kicks in and Squints makes his move, kissing her long and hard. Wendy is understandably angry, but as she tosses her little lover boy off the premises, it's impossible to see Squints as anything less than a hero. Even better, Wendy doesn't let the scene close on bad terms; when Squints presses himself up against the pool fence to catch one last look, she turns her cutting glare into a sweet smile and waves.