The Latest Rising Stars in Hollywood: Bookies

Rita Embry of Miami won $100 from an online bookie last week. The 25-year-old graphic designer wasn’t playing the ponies or betting on the NBA playoffs. She cashed in on a wager that “X-Men: The Last Stand” would take in more than $81.5 million its opening weekend.

Ashley Shiffrin, a 25-year-old paralegal who scans the entertainment odds during lunch breaks at the Manhattan law firm where she works, lost $50 at the same website, at betus.com, after she underestimated how many people would buy tickets to “X-Men.” But she figures she’s still ahead: A week earlier she won $132 by backing Taylor Hicks to become this year’s “American Idol.”

Then there’s Aly Lalani, a 30-year-old software marketer in Toronto. Having won $100 at betbet.com by taking “the under” on “The Da Vinci Code,” Lalani says, he’s hooked.

“They’ve turned me from a football and basketball bettor into a football, basketball and movie bettor,” he said.

Fans such as these are giving new meaning to the term “Hollywood player.” By putting their money where their entertainment hunches are, they are turning the weekend box-office derby -- once followed mainly by studio executives and accountants -- into a participatory sport.

Online entertainment betting, originally a novelty aimed at hyping the sports books during Oscar season, is on the rise. World Sports Exchange, which runs a gambling site at wsex.com, reports that its movie wagering volume jumped 26% last year. These days, the site takes $25,000 to $50,000 worth of bets on each weekend’s box-office results.

Other sites have seen surges in entertainment betting, as people wager on events including the Academy Awards and last week’s Scripps National Spelling Bee as well as on the not-so-private lives of celebrities.

The trend is partly an inevitable result of the growing number of betting sites that skirt U.S. laws by popping up in places such as Antigua and Costa Rica. (The Justice Department says online wagering violates U.S. law, but legal experts say it is unlikely bettors would be prosecuted.)

The popularity of such sites also reflects the global fascination with all things No. 1.

“Nobody seems to care about the old questions anymore: Is a film any good? Does it have cultural meaning?” said Robert Sklar, a cinema professor at New York University. “Now people ask: ‘Will it come in above or below the predictions?’ ”

Sklar thinks plain old publicity is part of what’s driving the shift from qualitative to quantitative cultural analysis. Once, most movie fans couldn’t have found out the estimated weekend grosses if their lives depended on it. Now there’s no escaping the box-office tallies.

Sites exploit the universality of this knowledge by playing on another fundamental human impulse -- the desire to win.

Bettors win or lose based on whether a movie grosses over or under its line for the first three days: When BetUs.com set the target on the latest “X-Men” at $81.5 million, for example, everyone who bet the “over” won when ticket sales in the U.S. and Canada reached $102.8 million.

For the sites themselves, which have long catered to male sports fans, offering odds on pop culture is a way to lure women. Embry, the Miami designer, said she first heard of the pastime when she teased a male friend for spending too much time betting on sporting events online.

“He was like, ‘What are you talking about? It’s not just sports -- you can bet on the sex of Angelina Jolie’s baby or whatever,’ ” Embry recalled. “It was kind of a dare.”

She didn’t bet on the gender of Jolie’s child with Brad Pitt, but she couldn’t resist putting her predictions to the test with the new “X-Men” film. And once she’d placed a $100 bet that it would exceed expectations, she felt invested in the movie’s success.

On opening night, Embry surveyed her local multiplex with satisfaction. “All the rows were packed with teeny-boppers,” she said. “I was like, ‘Fabulous!’ ”

The seeds of online box-office betting can be traced to 1997, when Century City-based Hollywood Stock Exchange began holding contests centered on movie grosses at its website, at hsx.com. To this day, however, the site’s players vie only for bragging rights and logo-emblazoned prizes, not real money.

In April 2002, World Sports Exchange became the first online bookmaker to offer regular box-office betting, posting a line of $36 million on “The Scorpion King,” starring Dwayne “The Rock” Johnson.

In the four years since, betting has expanded from the Rock to the ridiculous. At betonsports.com, players can try to predict, “What will happen to Ashton Kutcher and Demi Moore by the end of 2007?”

Favored at 2-1 odds: They’ll have a kid. Second choice at 5-1: They’ll get a divorce. Longshot players who see the couple starting a retirement home for Bruce Willis can get 50-1.

Shiffrin, the Manhattan paralegal, made her biggest score to date when Tom Cruise and Katie Holmes had their daughter April 18. Early last year, long before the pair announced Holmes’ pregnancy, Shiffrin wagered that the couple would procreate in 2006. When they delivered, she won $225.

Irregularities have tainted betting on some prerecorded TV shows, prompting bookmakers to take precautions.

In mid-April, Bodog.com halted wagering on who would win the CBS reality show “Survivor: Panama” after its bookies noticed an influx of $100 maximum bets on contestant Danielle DiLorenzo, then heard from a tipster suggesting that information on the finale had been leaked.

Similarly, in 2003, the site said its managers saw a series of suspicious “Survivor” bets, then learned that CBS staffers were driving the action.

They aren’t the only Hollywood insiders to get into the game.

World Sports Exchange says about 15 of its 200 entertainment-betting regulars are studio executives or producers. “The thrill of betting with ‘inside information’ must be irresistible,” said oddsmaker David Lee.

A movie producer who lives in Los Angeles, speaking on condition of anonymity for fear of potential legal problems, says he bets $20 to $50 at the site -- but only when the line looks beatable.

If the line on Pixar Animation Studio’s “Cars,” which opens this weekend, looks reasonable, he will pounce on the ‘over,’ he said, noting the studio’s success with titles such as “Toy Story” and “Finding Nemo.”

“I would not bet against Pixar,” he said. “They’re six for six at the box office and they have one of the most loyal fan bases outside of the ‘Star Wars’ series.”

Many box-office bettors do plenty of research.

For example, Lalani studied the track record of director Bryan Singer, whose hits include the first two “X-Men” films, before wagering $100 that Singer’s upcoming superhero sequel, “Superman Returns,” will bring in more than $90.5 million when it opens this month despite its relatively unknown star, Brandon Routh.

Shiffrin has $30 riding on this weekend’s romantic comedy “The Break-Up,” which she figured would go over its $29.5-million line. Her logic: Audiences would be curious to see the chemistry between stars Vince Vaughn and Jennifer Aniston, who are widely reported to be a real-life item.

Her wager looks like a shoo-in after Universal Pictures estimated a gross of $38.1 million on Sunday.

Embry, relying on reasoning of her own, appears set to win $25 after taking the same stance.

“Vince Vaughn is hysterical and has that whole frat boy following,” she figured, “so girls will probably be able to drag their boyfriends to see this one.”