WHEN HE SPLIT WITH TOUKIE SMITH, DE NIRO’S MIND was so far from thoughts of marriage that not even the birth of the twins changed it. However, a few years along into his fifties he did seem to be thinking about tying the knot again. At the time, he was seen around with Anne-Marie Fox, a onetime Playboy playmate who was just beginning a career as a publicity photographer on film sets; her first credited work along those lines, in fact, would be behind-the-scene shots from the making of Frankenstein, including many photos of De Niro at various stages of applying and removing his Creature makeup. In late 1995, New York newspapers reported that De Niro had bought a loft for Fox, who—younger than he, and African American—fit the profile of virtually every significant woman in his romantic life, and that marriage was in the air.

It wasn’t, though, nor was it the following year when, once again, a New York paper said that he’d be getting married the following week at Don Rickles’s house in Los Angeles. De Niro denied it and the paper retracted, but they insisted that De Niro had been discussing a wedding and had introduced people to a woman whom he’d identified as his fiancée. It wasn’t Fox, though. It was Grace Hightower.

De Niro and Hightower didn’t marry at the Rickles residence in 1996, but she did move into his Tribeca home with him—displacing Fox, in fact. De Niro and Hightower had known each other for nearly a decade at that point, since 1987, when he’d spotted her working at the New York restaurant Mr. Chow and passed a note to the owner asking if he could meet her.

She turned out to be an unlikely individual indeed. Born in 1955 as one of three girls in a family of ten children in Kilmichael, Mississippi (“a dot on the map 100 miles north of Jackson,” she explained), she was of African American and Blackfoot Indian heritage, at a time and a place when being a girl with those bloodlines was to have three strikes against you. Her parents were hardworking and instilled in their children a powerful ethic of self-reliance, resourcefulness, duty, pride, and honor. “We lived on a farm,” Hightower said years later, “of modest means, producing and eating nearly all that we ate. In fact, the only time we visited the supermarket was when we bought sugar. We worked the land, ate from the land, and became connected to the land.” Her dad, she recalled, taught her a singularly important lesson: “Never go to bed without paying your debts.”

But he also instilled in her a thirst to experience the world beyond the farm. She and her brothers used to thumb through an encyclopedia, dreaming of travel, and as soon as she was able she got out into the world to work and make fulfilling that dream possible. “I did everything,” she remembered. “I worked at S. S. Kresge, the five-and-dime. I worked in a mailroom. I worked processing insurance claims.”

By 1980, in her mid-twenties, she had managed to land a job as a flight attendant for TWA, based in New York. In that capacity, she was noticed by a pair of public relations executives for Saks Fifth Avenue, who hired her as a model. In 1982, she was among a group of young black men and women working in the airline industry to be profiled in Ebony. Soon after that, she changed her home base to Paris, living at the Hôtel de Suez on the Left Bank, taking French lessons, and trying to get started as, among other things, a mutual funds trader. When that line of work didn’t pan out, she came back to the States, winding up at Mr. Chow.

The first time she met De Niro, he didn’t, unusually, try to make a move on her; in fact, she had to tell him that his reservation had been lost. The following year, though, he did ask her out, and they began to see each other as he passed through London to work. “It was an ease-in,” Hightower explained. “It wasn’t a whirlwind.” Finally, in late 1995 she agreed to move back to New York and live with him.

The talk of De Niro and Hightower marrying came at almost the same time that he was quarreling in court with Toukie Smith over the care and custody of their twin sons. In the ensuing gossip conflagration, it was rumored that De Niro and Hightower (who had taken a hand in helping him parent the twins when they were in his care) wanted to start a family of their own. She was a good candidate, said De Niro’s chum Chuck Low, who called her “the most stable of [Bob’s] girlfriends.” But even though she was wearing a ten-carat emerald-cut diamond that was said to cost six figures and there were whispers that they had been working on a prenuptial agreement with their lawyers, they didn’t seem ready to pull the trigger.

Then in June 1997 Hightower phoned the Depuy Canal House restaurant in High Falls, New York, and made reservations for a large party on Tuesday the seventeenth. She ordered a five-course meal that included wakame and lobster in rice paper and poussin breast with cranberry quince stuffing, and she asked that the restaurant print up special menus that would read “Love, Bob and Grace.”

On the given day, De Niro and Hightower showed up at the restaurant at the appointed time, having been married a few hours earlier in a civil ceremony “somewhere in New York State,” according to his spokesman. The party, numbering around a dozen, included Joe Pesci, who had stood as best man, and Harvey Keitel. It was a week before word of the wedding trickled into New York City, taking many of De Niro’s closest associates by surprise. “He’s great at keeping details from his best friends,” Drew Nieporent told the New York Daily News.

Ten months later, almost as if it had been spelled out in their legal agreement, they welcomed a baby boy, Elliot, on March 18, 1998. De Niro was almost fifty-five; Hightower, who had taken the name De Niro, was forty-four. He now had five children (one adopted) by three women, and it looked for all the world as if his life and ways were finally settled.

MEANWHILE, PERHAPS INVESTED with a sense of urgency by a second marriage and growing brood of offspring, he ramped up his moviemaking work considerably—which was only possible, of course, if he put concerns about quality aside.

In the winter of 1994–95, with Casino and Heat coming into theaters, he was in Los Angeles and the Bay Area to make a new film, The Fan, based on a novel by Peter Abrahams about a baseball fan whose connection to a star player for the San Francisco Giants becomes obsessive and, finally, deadly. De Niro played the title character, a traveling knife salesman named Gil Renard whose broken marriage has left him with only baseball as a means to connect with his son. When their favorite player, Bobby Rayburn (Wesley Snipes), falls into a slump that threatens his spot in the lineup, Renard executes Rayburn’s would-be replacement (Benicio Del Toro) and then finally, completely psychotic, goes after Rayburn himself. On hand as well would be John Leguizamo as Rayburn’s agent and Ellen Barkin as a sharp-tongued talk radio host whose criticism of Rayburn incurs Renard’s wrath. Directing was Tony Scott, the hard-living, brassy visualist behind such commercial smashes as Top Gun, The Last Boy Scout, and Crimson Tide.

This was high-concept moviemaking, and De Niro was in it to get paid. Oh, he worked: he spent time going over the script carefully with Scott, recording their sessions, and suggesting changes to the character over a pile of transcriptions that ran to hundreds of pages; he interviewed cops and bodyguards about the phenomenon of stalkers; he spoke to a traveling knife salesman about the practices of his trade; he tapped his own experiences of being approached inappropriately by fans; he read up on Jeffrey Dahmer, David Berkowitz, Mark David Chapman, and various notorious celebrity stalkers; he even learned a little bit of knife throwing. But he was hardly stretching himself, merely reheating some bits of Travis Bickle and Max Cady.

There was a single memorable incident during production. A San Francisco cop stumbled across the set and, noticing the crew occupying a section of railroad line, interrupted shooting and ordered them off the tracks. De Niro, agitated, jumped behind the wheel of a Humvee that was part of the scene and gunned it around the traffic barricade, slamming to a stop just feet away from a passing train, then storming off to his trailer. When the cop declared that he was going to cite him for recklessness, De Niro sent his stunt double out to sign the ticket (the fine was $104), then emerged a few minutes later, shouting, “You don’t know what the fuck you’re doing!” at the officer.

Had anyone filmed that little bit of drama, it might’ve made for the most memorable thing in The Fan.

LORENZO CARCATERRA’S BOOK Sleepers seemed to many readers to be like a movie as soon as it was published in 1995. But that wasn’t necessarily a compliment: they were comparing it to a film because it seemed, frankly, fake.

Carcaterra, a reporter for the New York Daily News, had written a memoir of a harrowing passage of his youth, when, he said, he and three friends from the Hell’s Kitchen neighborhood of Manhattan were sentenced harshly for a prank gone bad and sent to an upstate New York reformatory, where they were brutalized and sexually abused by guards. Years later, Carcaterra and another of his chums had turned out well: a newspaperman and an assistant district attorney, respectively. But the other two had become criminals, and when they unexpectedly encountered the guard who’d been their chief tormentor in reform school, they killed him. The subsequent murder trial, Carcaterra said, had been manipulated by the defendants’ friends—the writer and the prosecutor—with the help of a parish priest who willingly perjured himself to help acquit the killers.

Ballantine Books published Sleepers as nonfiction, and it was a bestseller, but virtually from the start its veracity was attacked by prison authorities, the Manhattan DA’s office, the Catholic Church, and other reporters, who could find little or no evidence of any incidents that matched Carcaterra’s story. Carcaterra and his editors stood behind the book, saying that many details of date, place, name, and even incident had been altered to protect people but that the story was true in its contours and its themes. That may have been the case, but such incidents deeply dented the book’s credibility, and the author’s reputation never fully recovered.

None of that, of course, meant a thing to Hollywood: Sleepers was a sensational tale with an ensemble full of meaty roles, and Warner Bros. paid $2 million for the film rights after a bidding war. Barry Levinson was brought in to adapt the book and direct, and his cast included Brad Pitt as the young prosecutor, Jason Patric as the writer, Billy Crudup and Ron Eldard as the killers, Kevin Bacon as their torturer/victim, Dustin Hoffman as a boozy defense attorney, and, as the priest willing to perjure himself because he had known the quartet of boys when they were young, De Niro.

He had only a few scenes, but he took them seriously, studiously comparing the script to the book and trying to create a character who was partly fun-loving but essentially sober and unimpeachably decent. As he knew, “priests are not supposed to violate certain rules or certain laws, even if they are unspoken. But that does not mean that they can’t be broken if the priest feels it is morally right.” He accepted that Carcaterra’s account might have been fabricated: “It was hard to believe that the guards were so vile,” he said. But it didn’t finally matter. “I’m afraid I do believe it, because there are people like that.… If the abuse did not happen in this particular case, then it sure has elsewhere at some point.”

The controversy over the story’s veracity dogged Sleepers into theaters, and virtually every review took a stand on the question, usually scolding. Couple that with the deeply disquieting theme of child abuse, and no amount of star power could draw people into the theater. The one bright side: De Niro enjoyed working with both Levinson and Hoffman (“He really is terrific,” he gushed to a reporter); it wouldn’t be long before they tried it again.

SCOTT MCPHERSON’S 1991 play Marvin’s Room was a cri de coeur from the first decade of the AIDS plague, even though AIDS wasn’t explicitly a part of the story. It centers on two sisters whose father has been slowly dying after a stroke. One sister has cared for him for almost twenty years, but now she has leukemia, and she needs the help of her flighty sister, whose son has been institutionalized after deliberately burning down their house. McPherson wrote the play after caring for a partner who was dying of AIDS, and Tribeca Productions acquired the film rights in 1992, just as McPherson himself was dying of the disease. Jessica Lange was attached to play one of the sisters at that time, and De Niro was planning to produce it.

By the time it was made, in the late summer and fall of 1995, Lange was gone and De Niro had taken on a cameo as a physician with a goofball sense of humor and a contentious rapport with a colleague (Dan Hedaya). The sisters were played by Diane Keaton and Meryl Streep, the troubled son by Leonardo DiCaprio, and, in his final feature film performance, the dying man by Hume Cronyn. Jerry Zaks, best known for Broadway comedies and musicals, made his feature film debut as director.

The play had been dark (despite jagged bits of humor) and small, and it wasn’t obviously film material, a sense that was borne out after Zaks finished shooting it. There seemed to be no appropriate distribution moment: it would get lost in the summer and wasn’t quite powerful enough to be a serious awards season contender. It was released, finally, in February 1997, to modestly warm reviews and negligible box office.

IT WAS COMMONLY believed that De Niro and Martin Scorsese worked so well together because they understood each other’s essence and background so well, but that wasn’t entirely true. While De Niro had some firsthand knowledge of the Little Italy world of Scorsese’s youth, Scorsese could only imagine what De Niro’s childhood in the bohemia of the Greenwich Village art scene had been like. In 1996, though, De Niro met a director who, like him, had grown up in an artist’s household.

James Mangold was the son of two artists—the painters Robert and Sylvia Plimack Mangold. He was raised in the Hudson River valley north of New York and had attended film school at CalArts and Columbia University, where, under the tutelage of Milos Forman, he developed two scripts: a story of a sad, overweight loner, entitled Heavy, and a loose remake of High Noon set in the world of contemporary police corruption. Heavy had been Mangold’s debut and won him the Best Directing prize at the 1995 Sundance Film Festival. It brought Mangold to the attention of Miramax Films and Harvey Weinstein, and Mangold’s other script, now entitled Cop Land, was put into production.

On the heels of the massive success of Pulp Fiction, and especially the resurrected career of John Travolta, the idea of an ensemble crime story from Miramax was exciting enough to attract a number of top stars to at least consider the film, including Travolta, Tom Cruise, Sean Penn, even Tom Hanks. However, none of them proved willing to work for what the studio was hoping to pay for the lead role, a hapless cop who finds that he has a nest of corrupt New York City detectives running his small Catskills town like their personal realm. Instead, seeking to bring back another star of the 1970s whose career had faded into self-parody, Weinstein landed Sylvester Stallone. Around him, as corrupt cops, were Harvey Keitel, Ray Liotta (with Cathy Moriarty as his wife), and Robert Patrick, while De Niro had a key role as an NYPD internal affairs investigator trying to convince the small-town cop to help him make his case against the bad guys.

“We feel overwhelmed and blessed that Robert De Niro has joined this project with his enormous talent, integrity and brilliance,” Weinstein gushed to the press when it was announced that De Niro was in. He might later have wished that he’d tempered his words. Despite his association with De Niro and the Tribeca Film Center, Weinstein was the odd man out when De Niro and Mangold discovered the unusual coincidence of their parentage. “We both spent our childhoods at gallery openings,” Mangold recalled. They bonded as well in wanting to see Cop Land made as Mangold intended it and not as Weinstein, who had earned a reputation as a heavy-handed producer in the old-time Hollywood style, wished to see it. Mangold was pressured by Weinstein in matters of casting and in shooting an alternative ending (which Weinstein himself wrote), and in both cases Mangold turned to De Niro, who, much to Weinstein’s dismay, backed up the director’s vision and authority. Both times—including the new ending, which De Niro simply refused to show up to shoot, no matter the fee dangled in front of him—Mangold won out.

De Niro didn’t pour himself into the role. He’d played cops before, he knew the milieu, he trusted the director. He spent a little time boning up on the hierarchy of rank in the NYPD and on the off-duty lifestyle habits of cops, particularly the ones who chose to live outside the city. Otherwise, he knew he was merely a piece of the puzzle. The film shot throughout the summer and fall of 1996 and, after the typically protracted and painful Miramax editing process (not for nothing had Weinstein been nicknamed “Harvey Scissorhands”), it debuted the following summer to generally good notices and modest box office.

THE ONE INDISPUTABLY true thing to come out of Sleepers was the relationship that De Niro and Dustin Hoffman had forged in their few working days together. De Niro admired Hoffman’s breezy personal style—“I always envy the way he can speak and be funny and smart”—and he liked to remind Hoffman of their very first encounter, back in 1968, when Hoffman was a rising star and De Niro, six years younger, was a struggling actor serving him drinks and canapés at a Eugene McCarthy presidential campaign event.

It was presidential politics that would bring them back together, in a fashion. In 1996, with Sleepers in theaters, Barry Levinson and New Line Cinema acquired the rights to American Hero, a 1993 novel by Larry Beinert that proposed, with tongue in cheek, that President George H. W. Bush had started the first Gulf War as a means of inflating his approval ratings and increasing his chances of reelection. “What we were interested in was the blurring of the line between Washington and Hollywood,” Levinson explained. Screenwriter Hilary Henkin was called on to adapt the book, and then David Mamet was hired to punch up and energize her script. Late in the year, Levinson invited De Niro, Hoffman, and Anne Heche to a table reading of the most current draft, and they had a blast. As it happened, Warner Bros. was stalled on Levinson’s pricey sci-fi film Sphere, which would star Hoffman, and a window of a couple of idle months lay ahead. With less than $20 million of New Line’s money and a shooting schedule of less than thirty days, the three actors and Levinson agreed to go forward with the film, which had been retitled Wag the Dog.

De Niro was to play Conrad Brean, a political campaign strategist who has the luxury of a popular president running for reelection as a client. With a few short weeks to go before the election, however, and with the candidate abroad in China, a sex scandal breaks out involving the president and an underage girl whose youth group toured the White House. Called upon to distract the media from the ensuing firestorm, Brean hires Hollywood producer Stanley Motss (Hoffman) to stage a phony war in Eastern Europe, complete with fabricated atrocities and heroes, a theme song, a fad, and a logo. Heche was cast as the White House aide charged with riding herd on the pair of schemers, and Woody Harrelson, Dennis Leary, and Willie Nelson were among those with supporting roles.

De Niro was concerned that, despite the over-the-top nature of the story, there be an air of credibility throughout, and he sent the script to friends in the New York media, including Tom Brokaw of NBC and Judith Miller of the New York Times, to vet it for plausibility; he also asked for a review from veteran diplomat Richard Holbrooke. All three told him that the thing might be overly broad and was defiantly cynical but that there was a vein of realism in it. The film was shot in early 1997, just after the reelection of Bill Clinton, and, being a small movie with big stars, was released in late December, when film award talk was heating up—albeit on only three screens in New York and Los Angeles, to qualify for Oscar consideration.

It’s hard to see how anyone thought of De Niro to play the WASPy, donnish Brean, but he seems to love the role: the shabby, vaguely academic mien and wardrobe, the slippery logic, the nonstop motion and rat-a-tat patter. He plays it low-key and, indeed, low-fi, not trying to create a character so much as slip into the role unnoticed, rather as he had in recent years in the likes of Cop Land and Marvin’s Room. He carries much more of the film, though Hoffman is funnier by far and would be nominated for an Oscar (as, a bit curiously, Best Actor). There’s an ease and likeability to Brean: he appreciates the skill and energy of his colleagues. He relates beautifully to Motss in the way they talk, the way they seem physically relaxed around each other, the way their minds and skill sets meld. In reality, Brean is a bad guy, intent on fooling the public and corrupting the government for the sake of political gain. But De Niro plays him so offhandedly and agreeably that the audience can’t help but want him to succeed. Ultimately, Wag the Dog is remembered best for presaging eerily a real-life political drama, but it’s still, in the main, a film dotted with pleasures, and De Niro’s unaffected work serves it well.

The full release came a few weeks later, on January 11, and it made a respectable $7.8 million. And then, just one week later, a scandal involving Bill Clinton and a former White House intern, a young woman named Monica Lewinsky, stunned the world, leaking first on fledgling Internet-based news sites and then into the mainstream media, creating a long-running furor that ended in the impeachment of the president before the year was out.

It was a perfect instance of life catching up to art: among the commonly seen images of Lewinsky was one in which she wore a beret just like that sported by the underage girl in Wag the Dog. The tiny movie made on a lark had become synonymous with the juiciest presidential scandal since Watergate, and the film went on to play in theaters until spring, earning a healthy $43 million box office and Oscar nominations for Hoffman and the screenplay, and making the phrase “wag the dog” a kind of shorthand for the political use of media to distract the public from unpleasant realities.

DE NIRO CHOSE yet another ensemble role with his next picture, Jackie Brown, an adaptation of Elmore Leonard’s novel Rum Punch by writer-director Quentin Tarantino. De Niro was cast as Louis Gara, a newly minted parolee who’s back in business with his sometime partner in crime Ordell Robbie. Sloppy and out of sorts, Louis sits in quiet wonderment at the new world that has emerged during his years in prison: the technology, the sexual mores, the cat-and-mouse game with law enforcement. He was once sharp and dangerous, but incarceration has softened and neutered him, and even though Ordell wants to take him back on as a colleague, Louis needs more supervision than the services he can provide would seem to warrant.

Tarantino was an immense De Niro fan, both as a film buff and as an aspiring actor. “De Niro was it,” he once said. “He was who everyone in my acting classes wanted to be.” On British TV in 1994, not long before the release of Pulp Fiction, Tarantino provided introductions to a “Season of De Niro,” including airings of Mean Streets, Taxi Driver, Raging Bull, The Deer Hunter, and Once Upon a Time in America. Getting a personal hero into the film was a coup for the director, but it may have paled in comparison to the fact that his producer, Harvey Weinstein, let him fill the principal roles in the film with two nearly forgotten stars of the 1970s: Pam Grier and Robert Forster.

The mammoth success of Pulp Fiction meant that the follow-up would be gobbled up by the film press and audiences alike. But Tarantino chose, cannily, not to push the wild tenor of his previous films any further. Rather, Jackie Brown would be closer to a character study, the story of an airline hostess (Grier) coerced by law enforcement into turning against Ordell (Samuel L. Jackson) and using her own wiles and the help of a friendly bail bondsman (Forster) to keep herself alive and free.

De Niro, like Bridget Fonda, Chris Tucker, and Michael Keaton, was but a minor player in this deadly roundelay. As a result, he did very little work to prepare for the role. He grew out his hair and a goatee, he made a very few character notes in his script (“Do I smoke?… I’m trying to be hip, black … High now! Feeling good”), and he concentrated mainly on wardrobe. Nothing about Louis is stylish, but he does carry a sort of cool old-school vibe. To that end, Tarantino dressed De Niro in bowling shirts and Hawaiian shirts, some designed for the production, some of them vintage items from the director’s own closet. A few of those items were actually worn by De Niro in the film, but he and his director failed to bond over anything more substantial than shirts; rumors from the set indicated, in fact, that De Niro didn’t care for Tarantino’s manner and found the working environment uncomfortable.

That didn’t affect his performance. There’s humor and wistful sadness to Louis Gara. His post-prison manners are crude and simpleminded—one aspect of modern life after another causes him to revert to a watchful shell. He’s glad of Ordell’s solicitude, of the chance to get back on his feet, of the booze and weed and the minute or two of sex he’s granted by Melanie (Bridget Fonda), but the world outside prison confuses and scares him. Asked to do something simple by Ordell—to accompany Melanie to pick up a stash of money—he is out of his element and flustered; it takes only a few verbal goads for him to turn on Melanie and do something truly stupid and, in fact, unforgivable. His weakness and incapacity finally come to define him, and he becomes another employee Ordell must, in his phrase, “let go.” It’s a measure of the man that Louis used to be that Ordell is practically on the verge of tears when he does so.