At the time, Stallone had about as many hits under his belt as he had flops, and with the Rocky and Rambo franchises firmly in his rearview mirror (until, of course, the revival of both properties a decade later), his career was floating into uncertain waters as he started to take parts that played against his type as an uber-macho ass-kicker. He even took up voice acting in the bizarre DreamWorks movie Antz in 1998, which has to be a half-step above rapping in a fake Dunkin’ Donuts ad like Al Pacino did in Jack and Jill.
Smack dab in the middle of a career impasse, Rambo stepped into Macdonald’s firing line and took shot after shot from a bloodied Macdonald in the quintessential Norm Macdonald style that is so casually brutal to the targets of his jokes. But Rocky took it like a champ and played the perfect straight man as his life’s work was lampooned in front of a howling audience.
In all of Stallone’s comedy appearances, no one ever roasted him as viciously and as personally as Macdonald did that fateful Saturday night. The only other time Stallone was on the receiving end of a joke this harsh was when Arnold Schwarzenegger baited him into taking the leading role in Stop! Or My Mom Will Shoot.