Television ads promoting movies are not the normal business of politics or the courts, but they are this month because conservative activists are seeking a wide audience for "Hillary: The Movie."

David N. Bossie, who made a name for himself as a relentless investigator of the Clintons during the 1990s, has released a 90-minute documentary on the New York senator. His targets include not just her but the campaign-funding regulatory law known as McCain-Feingold, one of the signal legislative accomplishments of another presidential candidate, Sen. John McCain (R-Ariz.).

Bossie's group is challenging the law's limits on its efforts to promote the movie and has appealed to the U.S. Supreme Court. The litigation underscores the difficulty of drawing lines when money, politics and free-speech principles clash.

"Hillary: The Movie" includes a series of interviews with Clinton critics, including Ann Coulter, Newt Gingrich and Dick Morris. "If you want to hear about the Clinton scandals of the past and present, you have it here!," Citizens United, Bossie's group, says on its website.

The group, a nonprofit corporation, is free to promote its movie and sell DVDs on itswebsite. But one provision of McCain-Feingold makes it illegal to use corporate or union money for "any broadcast, cable or satellite communication" if it "refers to a clearly identified candidate for federal office" within 30 days of a primary election or a convention or within 60 days of a general election. That "blackout period," as it is known, has covered California and much of the nation for the last month as the primary elections were pending.

McCain and other sponsors of the bill wanted to stop the slew of corporate-funded broadcast ads on the eve of an election.

For more than a century, corporations have been barred from spending money to elect or defeat federal candidates. In the 1980s, however, the federal rules freed corporations and other groups to run "issue ads." In short order, these ads evolved into thinly veiled attacks that mocked a candidate's stand on an issue and urged viewers and the listeners to "send a message" to Sen. Smith or Rep. Jones.

The McCain-Feingold Act, which went into effect in 2002, was written broadly to bar such election-eve ads. It covered nonprofit corporations as well as moneymaking firms. And it was triggered by the mere mention of the candidate's name.

That posed an obvious problem for Bossie and his group:

"How can you advertise this movie without mentioning the name 'Hillary'?" asked James Bopp Jr., a 1st Amendment lawyer representing Citizens United.

In December, the group said it wanted to run 30-second ads on Fox News and other television outlets calling attention to the movie and went to court seeking an order that would shield it from the law. Bopp argued that what he termed "core political speech" deserved full free-speech protection under the 1st Amendment.

This is not a new argument for Bopp. Last year he won a major ruling in the Supreme Court that relaxed the ban on corporate-funded broadcast ads. In that case, he was representing the Wisconsin Right to Life Committee, a nonprofit group that wanted to broadcast radio ads urging its senators, including Russell D. Feingold (D-Wis.), to support President Bush's judicial nominees.

In a 5-4 decision, the high court said that such lobbying ads were protected. "The 1st Amendment requires us to err on the side of protecting political speech rather than suppressing it," wrote Chief Justice John G. Roberts Jr.

Now, Bopp is hoping to get the court's attention with "Hillary: The Movie."

But his chances may have been dimmed when he won a partial victory Jan. 15. A three-judge panel ruled that the movie itself is akin to a campaign ad and cannot be broadcast on television. It tells "the electorate that Sen. Clinton is unfit for office . . . and that viewers should vote against her," they said. However, they said that brief ads for the movie could be broadcast because "they proposed a commercial transaction -- buy the DVD of The Movie."

But in a third conclusion, the judges said the ads for the movie are still subject to the law, and Citizens United therefore must disclose who donated money to support the film.

The group has refused to accept that requirement, and Bopp has now asked the Supreme Court to intervene and to strike down the disclosure rules for political ads.

"If you must disclose your contributors, you are subjecting them to harassment and intimidation," he said. "It also chills their willingness to give money."

For his part, Bossie said, he was inspired by Michael Moore, a left-leaning filmmaker whose documentaries have targeted Bush, among others. "I saw the impact Moore was having. I realized the long-form documentary could be a powerful tool to deliver a political message," he said.

Bossie also sought to use the campaign laws against Moore. In 2004, he complained to the Federal Election Commission about Moore's film "Fahrenheit 9/11" because it was a political attack on Bush. It was also being advertised as the president ran for reelection.

Since Bush did not have to win in Republican primaries that year, the ad ban was not triggered until a month before the GOP convention. And just in time, Moore's lawyer told the FEC that ads for "Fahrenheit 9/11" would no longer mention or depict Bush. The FEC then voted to drop the complaint.

"This shows the danger of trying to regulate all these things," said Bradley A. Smith, a former FEC chairman and a critic of the campaign-funding laws. "Do we really want to go down the road of having a federal agency decide whether you can broadcast ads for a movie or a book?"

Still, some election-law experts doubt that the court will intervene in this case. "This does not involve a ban on speech," said Richard L. Hasen, a law professor at Loyola Law School in Los Angeles. "And I don't think there's an appetite for weakening the disclosure laws."

The high court will not consider the issue until mid-February. By then, the primaries in California, New York and many other states will be over. And for a time, Bossie and his group will be free to advertise their movie as they choose.

david.savage@latimes.com