By Alan Schroeder
Illustrations by Phil Wilson

On November 4, 1944, three days before his election to an unprecedented fourth term in the White House, Franklin Delano Roosevelt came to Fenway Park for the last big campaign rally of his career.

A day earlier, sound trucks had rolled through Boston's streets, beckoning everyone within earshot to come to the ballpark to "hear our great leader." Now, forty thousand Roosevelt fans jammed into Fenway, filling every seat and spilling out into the aisles. Fifteen thousand more listened to loudspeakers set up outside the gates.

An occasion this momentous demanded impressive warm-up talent. To fill the bill, FDR, an aficionado of all things show biz, enlisted two of the country's hottest young stars. Twenty-nine-year-old Orson Welles, boy wonder of radio and film, had campaigned tirelessly for Roosevelt throughout the fall, to the point of physical collapse. Frank Sinatra, a year and a half younger, had come into the fold in late September when FDR invited him to a White House tea. (Emerging from the mansion, the nation's number-one singing sensation recapped for reporters his conversation with the president: "He kidded me about making the girls faint and asked me how I do it. I said I wished to hell I knew.")

As the crowd awaited Roosevelt's arrival on this warm autumn night, the opening acts took the stage. Sinatra, at the height of his teen-idol glory, poured his golden voice into the national anthem. When female fans began to "squeal in delighted delirium," the Boston Herald noted, "their elders quickly shut them up."

Then the full-throated Welles presented his own specialty, impassioned political rhetoric. Six years earlier, the actor/director/writer/producer had scared the bejesus out of millions of radio listeners with his "War of the Worlds" broadcast. Tonight he spun a different horror story, a diatribe against FDR opponent Thomas Dewey. Reminding the audience of Adolf Hitler's dictum — tell big enough lies, and people will believe them — Welles charged that "the Republican presidential candidate follows Hitler's advice."

With spectators whipped into a frenzy, the stage was set for the leading man to make his dramatic entrance. "We want Roosevelt!" the crowd chanted. At the stroke of nine, they got their wish. While the band played "Hail to the Chief," FDR rode in a convertible from center field to the floodlit grounds.

The throng's roar drowned out the music and the first few sentences of the president's speech, which he delivered from the car, illuminated like an angel amid the bright white light. At the conclusion of his remarks, the crowd resumed its chant — "We want Roosevelt! We want Roosevelt!" For ten minutes, with the voices echoing all the way to the Back Bay, the president circled the ballpark in his convertible, like a slugger taking victory laps.

Standing in the shadows, Sinatra watched the old pro with admiration. "What a guy," he said. "And, boy, does he pack 'em in."

Every four years, like clockwork, Washington and Hollywood aristocrats join forces out on the campaign trail. Sharing the limelight at rallies and fundraisers, each group has something the other wants. Show business celebrities lend their glamour to less-than-scintillating officeseekers. Politicians confer intellectual legitimacy to a community that yearns to be taken seriously.

It's a pop-culture phenomenon, this ardent and sometimes awkward dance between presidential hopefuls and performing artists. But the relationship, as both candidates and entertainers soon discover, is complicated, and holds plenty of risks as well as rewards.

"He read Variety like I read Variety"

Actors campaigned for presidential candidates well before Franklin Roosevelt. In 1920, a troupe of Broadway performers traveled to Ohio to stage a musical rally in Republican nominee Warren Harding's front yard. Four years later, Calvin Coolidge summoned New York stage stars to a campaign breakfast at the White House.

Yet it took FDR, an unreconstructed movie fan, to fully apprehend the value of entertainers on the political circuit. He inspired an impressive roster of stars to volunteer their services as campaigners, including Sinatra, Welles, Humphrey Bogart, Katharine Hepburn, Groucho Marx, Lucille Ball, and dozens of other marquee attractions.

The rise of television as a mass medium, coupled with the attendant costs of advertising, helped intensify the politics­show business relationship. By Dwight Eisenhower's 1952 presidential campaign, entertainers were playing more of a pecuniary role, along with their ornamental one.

If Eisenhower was the first president to systematically dip into deep celebrity pockets, his successor refined the art of deploying stars as campaigners. John F. Kennedy knew how effective celebrities would be in attracting money, crowds, and media attention.

Drawing on his family's long-standing ties to Hollywood — ranging from father Joseph P. Kennedy's stint as a movie mogul, to celebrity brother-in-law Peter Lawford — JFK sprinkled his 1960 campaign with silver-screen glitter. Actors appreciated that Kennedy, like Roosevelt before him, was a genuine movie fan, who spoke fluently the language of entertainment. As Lawford described JFK, "He read Variety like I read Variety."

Kennedy star power loomed large during the 1960 Democratic National Convention, fortuitously held in Los Angeles. Sinatra, Janet Leigh, Tony Curtis, Sammy Davis Jr., Nat King Cole, Judy Garland — all took part in high-profile convention-week events that glamorized the prosaic rituals of politics. Sinatra and Leigh even worked the convention floor like veterans, chatting up delegates and promoting Kennedy to willing journalists.

During the general-election campaign, Kennedy limited his appearances with movie stars, fearing too much chumminess might be unseemly. He did turn up at celebrity-studded rallies in New York and Los Angeles, though, and also played second banana to singer Harry Belafonte in an unusual campaign ad. Aimed at African-American voters, the TV spot had JFK mostly listening while Belafonte, "as a Negro and as an American," pleaded the candidate's case for him. In other radio and TV commercials, celebrities such as Lena Horne, Milton Berle, Gene Kelly, Henry Fonda, and Myrna Loy made the Kennedy pitch solo.

Kennedy's success with using celebrities in his campaign begat a series of glittering fundraisers scattered throughout his three-year presidency, which channeled millions of dollars into Democratic coffers. The most legendary took place in May 1962 at Madison Square Garden, where Marilyn Monroe sang her indelible rendition of "Happy Birthday, Mister President." (Ever the good soldier, Monroe even paid for her own thousand-dollar ticket.) JFK, who closed the program, quipped, "I can now retire after having had ‘Happy Birthday' sung to me in such a sweet, wholesome way."

A year later, Kennedy journeyed to Los Angeles for a different kind of fundraiser, an intimate thousand-dollar-a-plate dinner for a hundred people, including Marlon Brando, Cary Grant, Burt Lancaster, Charlton Heston, Gene Kelly, Dean Martin — even Jack Webb, who played Sergeant Joe Friday on Dragnet. Instead of offering a formal speech, the president table-hopped, impressing his guests with a wide-ranging knowledge of movies in general and their careers in specific.

As Kennedy chatted with Rock Hudson — real name: Roy Fitzgerald — the conversation turned to their shared Irish ancestry. "You know all us Fitzgeralds are related, right?" JFK asked.

"That's right, sir," Hudson replied. "And I'm sure Ella will be happy to hear about it, too."

The great ideological divide

Until Bill Clinton burst onto the scene in 1992, Hollywood's love affair with John Kennedy knew no equal. Personalities aside, this lull in affection was at least partly attributable to the social and cultural upheavals of the 1960s and 1970s.

By the mid-1960s, with the collapse of the Hollywood studio system complete, actors were much freer to exercise their professional — and political — independence. And as performers grew ever more outspoken in their criticisms, particularly of the Vietnam War, relations between Washington and Hollywood soured.

To the surprise of few, Richard Nixon's notorious "enemies list" featured a host of actors, from the predictable assortment of liberals (Gregory Peck, Barbra Streisand, and Shirley MacLaine) to less ideological figures (Steve McQueen and Carol Channing). Paul Newman, who spent much of 1968 campaigning on behalf of presidential candidate Eugene McCarthy, called landing on the enemies list his "single highest honor. . . . All the other actors were so jealous."

On the other hand, post-Watergate campaign-finance reforms inadvertently sparked a fresh demand for entertainers out on the stump. Because the new rules encouraged small contributions, selling tickets to music concerts became a money-starved campaign's favorite fundraising mechanism.

The series of performances Warren Beatty produced for George McGovern in 1972 certified the value of entertainers as cash cows, with blue-chip headliners like Streisand, James Taylor, Carole King, and Simon and Garfunkel raking in more than a million dollars. (In the current campaign season, Streisand, Taylor, and King have all performed for candidate John Kerry.)

As the examples suggest, Democrats have had considerably more success than Republicans in recruiting entertainers to the hustings. Oddly, this imbalance was not much improved by the Ronald Reagan presidency. Despite Reagan's unique credentials as a Hollywood actor, none of his runs for office leaned heavily on the entertainment community.

To some extent, this was a deliberate tactic. As late as 1980, after Reagan's two terms as California governor, internal polling showed one in ten voters still viewed him primarily as an actor. But Reagan's bigger show-biz problem was his political philosophy, which tilted too far right to suit Hollywood's mostly liberal denizens. From the moment the former leading man first threw his hat into a ring, fellow actors showed as much willingness to campaign against him as for him.

"I know I could play the role of a governor," said Gene Kelly in a 1966 anti-Reagan commercial aired during the candidate's first bid for office, "but that I could never really sit in his chair and make decisions affecting the education of millions of children." Reagan's opponent, incumbent governor Edmund "Pat" Brown, took the argument a step further, reminding Californians that Abraham Lincoln had been shot by an actor.

By the time he ran for president, Reagan had attracted more enthusiastic show-business support, particularly from his contemporaries. Frank Sinatra, who sang for Roosevelt at Fenway Park in 1944, returned to Boston thirty-five years later to headline, along with Dean Martin, a fundraiser that netted the Reagan campaign $200,000.

Before the show, the candidate and wife Nancy joined the stars for a freewheeling backstage press conference that illustrates the extent to which entertainers are from Venus and politicians from Mars. When a reporter queried Reagan about his fundraising plans, a jocular Martin butted in: "I don't think that's any of your business."

Another journalist asked Reagan, "What cabinet posts have you promised these guys?" Sinatra's response: "Liquor."

In fact, President Reagan would give Sinatra the very thing John Kennedy had failed to deliver twenty years earlier — White House access. In addition to receiving frequent invitations to private functions at the mansion, Sinatra served as the administration's official impresario, producing the two inaugural galas and selecting entertainers for state occasions (the singer booked himself into the East Room twice).

In 1985, the president awarded Sinatra the Medal of Freedom, the nation's highest civilian honor. Mother Teresa was a co-recipient.

Mr. Clinton goes to Hollywood

Reagan and Sinatra's relationship demonstrates how high-profile entertainers can leverage their campaign contributions — monetary and otherwise — into social validation at the world's most exclusive address. And in recent decades, as entertainers give candidates more of their time, talent, and money, their expectations have increased.

The Bill Clinton presidency offers a fascinating study of the pros and cons of show-business support. After Clinton wooed and won the entertainment community during his first campaign, the lavishness of his inaugural festivities indicated diplomatic relations between 1600 Pennsylvania Avenue and Hollywood would continue to be cozy indeed. Drawn by a mind-numbing round of gala events spread over several days, a constellation of stars — everyone from Michael Jackson to Macaulay Culkin, Bob Dylan to Lauren Bacall — descended on the capital.

With so many egos jockeying for position at so many performances, tension could not help but prevail. "Some of these people believe they should be holding the Bible," an inaugural planner kvetched to the New York Times. "You have no idea."

During his first few months in office, Clinton seemed unable to wean himself away from the big names who had backed him. The new president dined with Paul Newman and Joanne Woodward. He went jogging with White House guest Judy Collins. He took Barbra Streisand to the Gridiron dinner. During a break in talks with Russian president Boris Yeltsin, he had coffee with Richard Gere, Cindy Crawford, Sharon Stone, and Richard Dreyfus; Gere used the occasion to lobby Clinton to meet with the Dalai Lama.

When a troupe of pro-Clinton actors came to Washington to promote a film that dealt with environmental issues, they received not only personal greetings from the president and the vice president, but a White House briefing from the secretary of the interior.

Then, in May 1993, something as mundane as a haircut sparked a public backlash to the entertainer overdose. During a California visit, Clinton got a trim from Beverly Hills stylist-to-the-stars Christophe onboard Air Force One, while it sat on a Los Angeles International runway. Journalists noted the haircut had idled the airport and inconvenienced thousands of travelers.

The president's critics pounced. "When you've got a different movie star in the White House every night," chided Ross Perot, "and you've got somebody up there from Hollywood pleading the case for the Dalai Lama, the average hard-working American in work clothes can't relate to that."

In a town-meeting appearance televised on CBS, Clinton defended himself, calling the haircut episode "a boner" and "a blowup." "I mean, look, I wear a forty-dollar watch," he told the studio audience. When a questioner suggested the president seemed "a little infatuated with Hollywood and celebrities," Clinton flatly denied he had "gone Hollywood": "The answer to that is no; heck, no; never, no. Never. Never."

Still, the impression lingered. A Washington Post columnist offered the White House some unsolicited advice — "If Clinton wants to see some Hollywood stars, he could do what the rest of us do: Go to a movie."

Trouble on the trail

In the wake of the controversy, Clinton briefly stopped making public appearances with entertainment luminaries. But this starstruck president could resist Hollywood no more than Hollywood could resist him. Throughout his eight-year tenure in office, actors, musicians, and comedians ranked among his most reliable partisans, campaigning at his side, showering him with cash, and standing steadfast during the dark days of impeachment.

By all accounts, Clinton genuinely enjoyed his celebrity associates. But in the eyes of the body politic, the friendships never quite shed the aura of quid pro quo. The haircut flap was followed in 1997 by the Lincoln Bedroom "scandal," the revelation that dozens of

entertainment-industry insiders who had made campaign contributions were treated to overnight stays at the White House. Even as the Clintons prepared to leave the mansion, new information surfaced about the valuable gifts they had received from such famous pals as Jack Nicholson and Steven Spielberg.

Bill Clinton learned what every president learns: Politicians who mix with performers run the risk of getting burned. The danger intensifies on the campaign trail, where visibility is high and entertainers don't necessarily understand the rules of the game. In 1992, President George H. W. Bush enlisted Gerald McRaney, star of the military-themed TV comedy Major Dad, for a swing through Florida. After the actor used his platform to denounce Clinton's lack of military service, the press reported McRaney had himself managed to avoid Vietnam duty.

True to form, this year's presidential campaign is again proving that celebrities can make their candidate's life difficult. John Kerry found himself on the defensive after Whoopi Goldberg delivered a raunchy anti-Bush comedy routine at a Democratic fundraiser in New York City. At the end of the show, the candidate compounded the problem by remarking, "Every performer tonight conveyed to you the heart and soul of our country." Republicans rushed to denounce Kerry's ties to Hollywood's "cultural elite."

Filmmaker Michael Moore sparked a controversy for Wesley Clark shortly before the New Hampshire primary. Appearing with the general at a rally, Moore called President George W. Bush a "deserter," a characterization Clark repeatedly declined to refute. As a result, at a crucial point in Clark's campaign, media attention shifted away from his message and onto Moore's rhetorical excesses.

More typically, though, entertainers involved in the 2004 campaign have done what they do best: raise money by putting on a show. Like many a Democrat before him, John Kerry has generated support from a vast array of performing artists, from rock (Jon Bon Jovi) to country (Willie Nelson), comedy (Billy Crystal) to drama (Dustin Hoffman).

By contrast, President Bush boasts fewer entertainment alliances than any candidate since Herbert Hoover. His biggest-name celebrity campaigners in 2000: Bo Derek and Wayne Newton. Even Richard Nixon had more friends in Hollywood.

Though entertainers make varied contributions to presidential campaigns, both Republicans and Democrats underutilize performers in what would seem a natural role — as talent coaches. A rare exception? Consummate show-biz connoisseur Franklin Roosevelt.

Orson Welles, who helped prep FDR for a 1944 campaign speech, marveled at his pupil's willingness to take direction. Shortly after the president delivered the address, he telephoned Welles, who had listened in via the radio, for an instant review.

"He asked me, ‘How did I do? Was my timing right?'" Welles recalled. "Just like an actor!"

Alan Schroeder, an associate professor in the School of Journalism, is the author of Celebrity-in-Chief: How Show Business Took Over the White House (Westview Press, 2004) and Presidential Debates: Forty Years of High-Risk TV (Columbia University Press, 2000).