Uncle Buck (1989)
If there's only one thing to say about Uncle Buck, it might be this: two unforgettable Johns gone too soon. Hughes wrote and directed John Candy (who he'd worked with in Planes,Trains and Automobiles) in this hilarious and heartwarming comedy about an unemployed slacker who babysits his nieces and nephew for a weekend. Hughes had an uncanny ability to home in on the hilarity of everyday interactions, and never is he so spot-on as in the rapid-fire interaction between Uncle Buck and his nephew, Niles (a pre-stardom Macauley Culkin). Just thinking about their chemistry—"What's your record for consecutive questions asked?" "Thirty-eight."—has us chuckling and longing for a giant pancake. But this film wasn't just about the laughs. Like Hughes himself, Buck put the unconditional love of family—with all its wacky uncles and brooding teens—first.