Yesterday, I watched the interview of Billy Crystal on The Daily Show and aside from the startling reminder of just how funny Crystal is as he approaches his 65^th birthday, I was deeply effected by a story he told.

In his earliest days as a standup, he performed one night at Catch A Rising Star, where he absolutely crushed his audience—20 minutes of pure gold. And yet, when he had dinner later that night with Jack Rollins, the man who discovered Woody Allen and made him a star, Rollins was unimpressed with Crystal’s set. This drove Crystal crazy and when he finally worked up the courage to ask why, Rollins complained that Crystal had played it safe.

Crystal’s entire set, he explained, was material that he knew would be appreciated by his audience, and Rollins acknowledged it was funny. But it also left him cold, as it told him nothing about the man behind the humour. It said nothing about who Crystal was and what he thought about the world.

Never be afraid to bomb, Rollins advised Crystal, and it has been Crystal’s advice to aspiring comics ever since.

Too often, writers of all media and genres face the same challenge. With an eye to being popular (liked) and commercial, we play it safe. We don’t push ourselves, our talents, or our audiences hard enough. We hold back for fear of offending. The results are shelves of books and DVDs that are milquetoast, bland, generic, and channels that are devoid of anything stimulating.

It’s not entirely the writer’s fault. Some of us have agents and managers cautioning us before the next deal. Editors and producers “honing” and “refining” out creativity in the hope of better numbers. But we let them do this to us and to our Art. Playing it safe may get you that next deal, but will it keep the deals coming?

When your work reads like the next writer’s work, which reads like the last writer’s work, why does anyone need to choose you or your idea?

Like them or no, there is no denying the talent that went into shows like The Big Bang Theory (4 physicists and an actress?), Breaking Bad (a meth-cooking school teacher?) and The Big C (a cancer comedy?). Or the book 50 Shades of Grey (mom reads porn?). Or the movie Memento (an inside-out movie?).

None of these were safe choices. None of these was obvious. All of these made people uncomfortable.

Go to the edge with your writing. Stare down the precipice and smile.

Don’t just face your fears; laugh at them and then take a giant step forward into the unknown.

In life, safe is an illusion. In Art, it is a lie.

As an artist, the most dangerous thing you can do is play it safe.

(Image is property of owner and is used here without permission because I like to live dangerously.)