The Adam Sandler movie "Jack and Jill" won in every category at the Razzie awards.

It's a record that can only be equaled, never exceeded (unless they add new categories). 

Among the "wins" for Sandler: Worst Picture, Worst Actor (for Sandler's work in "Jack & Jill" and "Just Go With It"), Worst Actress (as "Jill"), Worst Supporting Actor (for Al Pacino's cameo as himself), Worst Supporting Actress (for pal David Spade as "Monica"), Worst Screen Ensemble (for the entire cast), Worst Director (Dennis Dugan for "Jack and Jill" and "Just Go With It"), Worst Remake, Rip-off or Sequel ("Jack and Jill" for ripping off Ed Woods' camp classic "Glen or Glenda"), Worst Screen Couple (Sandler and Katie Holmes, Sandler and Al Pacino or Sandler with himself) and Worst Screenplay.

Yeah, Sandler won in both the actor and actress categories, but I think the funniest thing there is that Al Pacino won Worst Supporting Actor when he was playing the role of himself. How can you screw up playing yourself? Ah! That seems like a deep and metaphysical question. It reminds me of the notion that made André Gregory cry, as described by Wallace Shawn in "My Dinner with André":

The reason I was meeting André was that an acquaintance of mine, George Grassfield, had called me and just insisted that I had to see him. Apparently, George had been walking his dog in an odd section of town the night before, and he'd suddenly come upon André leaning against a crumbling old building, and sobbing. André had explained to George that he'd just been watching the Ingmar Bergman movie Autumn Sonata about twenty-five blocks away, and he'd been seized by a fit of ungovernable crying when the character played by Ingrid Bergman had said, "I could always live in my art, but never in my life."

But let's check YouTube for what Pacino actually did in the movie "Jack and Jill." Here:



Pacino's got the perfect lines, revealing that Sandler, et al., knew their movie was perfectly bad:

"Burn this. This must never be seen... All copies! Destroy them!"