Al Pacino. Total legend. “The Godfather,” “Serpico,” “Dog Day Afternoon,” “Scarface,” “Heat,” “Carlito’s Way,” and of course, “Jack and Jill.”
Pacino played himself in “Jack and Jill,” a debauched 2011 Adam Sandler comedy. Sandler, in drag, catches Pacino’s eye in the film — he’s smitten by her. Lust has no bounds, and Pacino becomes unhealthily obsessed, going to great lengths to lure Jill into his web.
It’s not like this was a cameo role either — Pacino played a significant role in the movie, with plenty of screen time. It’s one of the most dumbfounding — and unintentionally hysterical — bits of casting of the 21st century.
Thirteen years later, and “Jack and Jill” is still noteworthy as the moment Pacino finally succumbed to low brow filmmaking. People get involved in Sandler movies for a variety of reasons: many are friends of the actor, others just want the paycheck. For Pacino, it seems to have been the latter.
Speaking to the New York Times, Pacino admits that he only hopped onboard “Jack and Jill” because he was flat broke, screwed over of his assets by his “money manager,” who was found guilty of defrauding him and dozens of other celebrities.
“Jack and Jill.” I think that’s funny. It came at a time in my life that I needed it, because it was after I found out I had no more money. My accountant was in prison, and I needed something quickly. So I took this.
Pacino is said to have lost millions because of the Ponzi scheme and he was so desperate that there was no other choice than to star in “Jack and Jill.”
Pacino’s attempted molestation of a much larger Adam Sandler in wig and dress is something that I’ll never be able to erase from my memory. Yet Pacino never phoned it in. Being the absolute legend that he is, he gave the most committed performance I’ve ever seen in any Adam Sandler comedy. Inexplicably, and undeservedly, he also ended up winning the Razzie for Worst Supporting Actor.