WHEN BILLY CRYSTAL TURNED 40, HE WASN’T HAPPY about it. “I was gripped by a very cloudy mood,” he wrote in his 2013 memoir, Still Foolin’ ’Em. So he did what comedians do when faced with anxiety: He set out to find the humor beneath the heartache.
First would come his hilarious star turn as what the Los Angeles Times called “a reluctantly romantic leading man” in 1989’s When Harry Met Sally. Then he hit on a winning idea for what would become another iconic role.
“City Slickers,” he scribbled. “Three friends go on a fantasy cattle drive” — a metaphor for what was missing in their lives. “My character, like me, in his. In 1991, would become another huge hit for Castle Rock, grossing $180 million on a $26 million budget.
