Can Mark Cuban sing and dance?

But are these people capable of coming up with the next "Happy Gilmore"?

The convergence of technology and entertainment has spawned a new breed of executive: the tech film producer. Billionaire entrepreneur Mark Cuban has helped bring "Good Night, and Good Luck," touted as an Oscar contender, to the big screen, and soon you'll see his name in the credits on "The World's Fastest Indian," about an aged motorcycle racer played by Sir Anthony Hopkins. Cuban's production company will also release "Bubble," a Steven Soderburgh movie, simultaneously to the Web and to his Landmark theater chain this week.

eBay founder Jeff Skoll, meanwhile, put up some money for "Syriana" and "North Country." Google founders Larry Page and Sergey Brin will invest in "Broken Arrows," a sci-fi thriller written and directed by their Stanford pal Reid Gershbein.

In some ways, the trend is inevitable. Movies cost millions of dollars to produce, so who better to cover the cost than bachelor billionaires? Besides, it comes with loads of cachet and style. Dumping millions into David Yang's Steak Barn just doesn't seem as good a path toward crafting a jet-set image.

Throughout history, wealthy patrons have played a key role in the arts. After inheriting his parents' tool-making company, Howard Hughes moved to Hollywood to crank out "Hell's Angels" and "Scarface." And when Italian banking heir Lorenzo De' Medici wanted to increase Florence's influence, he became a sponsor of the cutting-edge artists of the day. Beethoven, Mozart, Voltaire--they all had rich friends. It didn't become hip to be impoverished as an artist until the Impressionists gained hold.

It would also be tough to do significantly worse than the film studios these days. Look at what is coming for the summer: a remake of the "The Poseidon Adventure" (with neither Shelley Winters nor Red Buttons), a movie rehash of TV's "Miami Vice," and the third edition in the "Mission Impossible" series. A big-screen version of "The Sanford Arms" can't be far behind.

But those dopey movie titles underscore an uncomfortable truth. Entertaining people is hard work, and it doesn't follow conventional formulas. Who would have thought, before the fact, that "Showgirls" would become enshrined as a cult classic?

Conversely, try to name the movie that won the Academy Award for best picture in 1993 off the top of your head? Critics hailed it as timeless at the time, but the name probably doesn't pop up instantly in your mind. (It was "Unforgiven.")

It's no easier to pinpoint a timeless classic in music. Need an example? "Cold-hearted orb that rules the night/Removes the colors from our sight." If you took art class in junior high sometime in the mid '70s, you probably have that Moody Blues song committed to memory.

The unpredictable nature of the entertainment industry goes a long way to explaining the reason film and music executives have a reputation for being surly and pushy. They live in a chaotic world where standards don't apply. You have to be willing to latch onto any idea that crosses your desk: convenience store clerk becomes prince of small Eastern European country; Martin Lawrence gets a job in a bioweapons facility; Lassie, but with a chimp. "The Importance of Being Ernest Saves Christmas"? Any one of these could be box-office hits.

Which brings me back to the first point. Tech execs have escaped from the cheesy milieu of Americana that the rest of us wallow in at least part of the day. They live in a world where wealthy, talented people contemplate whether human gene sequences can be patented or the societal aftereffects of capital gains cuts. In other words, they might be way too high-minded for the average American knucklehead. It's not like aliens from Neptune are the ones driving up the ratings for "Dancing with the Stars," after all.