Crystal believes he came close a couple of times, first for 1989's When Harry Met Sally, then with City Slickers in 91.
"I was mad at myself for getting sucked into the hype," says Crystal, whose latest film, Parental Guidance – a comedy in which a couple collide with their daughter over how to bring up the grandkids – is out next week.
"It's not a great goal of mine," he said.
Crystal, 64, has hosted the Academy Awards, watched by a global audience of 1billion, nine times, earning plaudits for his opening comedy medleys, skits and film montages.
His most recent stint as Oscars host was in February, though he faced criticism for lacking originality.
"The world is watching and the world is a rough room, so you can't please everybody!" says Crystal, who studied TV and film direction under Martin Scorsese at New York University before trying his hand at stand-up.
"I remember when Lord Of The Rings swept everything and the show got dull – because they were winning everything – and they blamed me! It's always the host's fault and it's not fair!"
But he added of his role: "It's a lot of work but a fun night."
Affable as Crystal is, you sense his frustration at a certain lack of freedom while filming Parental Guidance.
"When I was on my own making movies for Castle Rock Entertainment, you were just trusted and it was great," he said.
"Now there are more and more people involved in the process than ever before and I really hated that.
"There were mid-level executives in the ear of director Andy Fickman, director and the production team, with notes from the studio and concerns from Walden Media and Fox about how to make the movie.
"These constant notes, this constant pleasing a board of people about how you make a movie - I wasn't used to it.
"But we ended up getting used to it," he adds.
In Parental Guidance, Crystal plays Artie, a grumpy baseball fan who's married to Diane, played by Hollywood legend Bette Midler.
"Bette and I have known each other a long time but had never worked with together before.
"We both have a respect for the performers we grew up with. It's an old form of show business that unfortunately doesn't exist any more, and in that way we're throwbacks in the best way."
The script originated from Crystal and his wife Janice's own experiences looking after their grandchildren.
"It was great but exhausting and on the seventh day I rested, then came into the office and went: 'OK, here is the movie'."
Parental Guidance marks Crystal's first major movie role since 2002's Analyze That, the sequel to 1999's Analyze This.
Next year he'll promote Monsters University, a prequel to the phenomenally successful animation Monsters, Inc.
So Crystal remains positive about the future, saying: "I've always loved what I'm doing and what I will be doing - because there are still new things to find entertaining."
n Parental Guidance is in cinemas on December 26.