Justin Timberlake on fatherhood, his uncertain future and being best friends with Jimmy Fallon


Justin Timberlake is remembering the very first time he got chased by a mob of shrieking teenage girls.

"I was about 15 or 16 years old," he says. "We'd just given a concert in Germany at a festival on this huge field. And we were in the tour bus afterward, driving on a dirt road, and I looked out the window and saw all these young, impressionable females running after the bus." He shrugs his shoulders and gets to the point of the story: "I think we can all agree that I did not have a normal childhood."

Twenty years later, at age 36, Timberlake is having an unusual adulthood as well. At the moment, he's lounging at a corner table at the bar in the Chateau Marmont, his still-babyish face half hidden behind a scruffy beard and a black wool cap. Timberlake has been so famous for so long — as the youngest member of the wildly successful 1990s boy band NSYNC, as a multiplatinum Grammy-winning solo artist (26 million albums sold) and, increasingly, as an accomplished screen actor (he'll be co-starring with Kate Winslet in Woody Allen's next movie) — that he's learned to wear his celebrity like a pair of comfy old hammer pants. Indeed, he only can barely recall a time when he wasn't dodging paparazzi and making headlines for things like dating Britney Spears (and making a music video about their breakup) and accidentally setting off Janet Jackson's "wardrobe malfunction" at Super Bowl XXXVIII (even today, not a topic he's eager to talk about).

"I have some faint images from my childhood," he says matter-of-factly, sipping a beer, "but no, I can't really remember not being famous."

See photos of Justin Timberlake through the years:

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Justin Timberlake through the years
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Justin Timberlake through the years
Justin Timberlake during N'Sync London show case 1997 at L'Equipe Anglaise in London in London, United Kingdom. (Photo by Fred Duval/FilmMagic)
Justin Timberlake (Photo by Jeff Kravitz/FilmMagic)
LOS ANGELES - JANUARY 11: Singer Justin Timberlake of NSYNC attends the 26th Annual American Music Awards on January 11, 1999 at the Shrine Auditorium in Los Angeles, California. (Photo by Ron Galella, Ltd./WireImage)
LOS ANGELES - AUGUST 1999: Justin Timberlake from pop group *NSYNC, poses for an August 1999 portrait in Los Angeles, California. (Photo by Bob Berg/Getty Images)
NETHERLANDS - CIRCA 2000: Photo of Justin TIMBERLAKE and N' SYNC; Justin Timberlake posed in The Netherlands circa 2000. (Photo by Michel Linssen/Redferns)
Justin Timberlake during *NSYNC Visits Disney World - Candids and On Stage at Disney World in Orlando, Florida, United States. (Photo by James Devaney/WireImage)
Justin Timberlake (Photo by Jim Smeal/WireImage)
07/25/00 New York City 'NSYNC' unveils their new look-alike marionette dolls at FAO Schwarz toy store. Justin Timberlake with his doll. Photo by Evan Agostini/ImageDirect
NEW YORK CITY - JULY 31: Singers Justin Timberlake, Joey Fatone and Lance Bass of NSYNC attend the 'Coyote Ugly' New York City Premiere on July 31, 2000 at the Ziegfeld Theatre in New York City. (Photo by Ron Galella, Ltd./WireImage)
Justin Timberlake (Photo by Ron Galella, Ltd./WireImage)
BEVERLY HILLS, CA - FEBRUARY 20: Singer Justin Timberlake of NSYNC attends the 43rd Annual Grammy Awards Pre-Party Hosted by Clive Davis on February 20, 2001 at the Beverly Hills Hotel in Beverly Hills, California. (Photo by Ron Galella, Ltd./WireImage)
Justin Timberlake (left) and Chris Kirkpatrick of 'NSYNC on the 'mtv ICON: Janet Jackson' show taping at Sony Pictures Studios in Los Angeles, CA., March 10, 2001. (FrankMicelotta/ImageDirect)
(EXCLUSIVE, Premium Rates Apply) Britney Spears and Justin Timberlake (Photo by Kevin Mazur/WireImage)
Justin Timberlake during The 7th Annual Blockbuster Entertainment Awards - Arrivals at Shrine Auditorium in Los Angeles, California, United States. (Photo by SGranitz/WireImage)
Britney Spears and Justin Timberlake (Photo by KMazur/WireImage)
Lance Bass & Justin Timberlake during Top stars join *NSYNC for the 3rd annual Challenge for the Children basketball charity event, featuring celebrity team challenges and half-time performances. All proceeds go to children's programs and charities. in Las Vegas, Nevada, United States. (Photo by KMazur/WireImage)
Justin Timberlake at the The Metropolitan Opera House at Lincoln Center in New York City, New York (Photo by Kevin Kane/WireImage)
UNITED STATES - NOVEMBER 06: Britney Spears and boyfriend, 'N Sync's Justin Timberlake, arrive at Centro-Fly for a party marking the release of her new album, 'Britney.' (Photo by Richard Corkery/NY Daily News Archive via Getty Images)
Justin Timberlake arriving at the 2001 Billboard Music Awards in Las Vegas. (Photo by SGranitz/WireImage)
(NO TABLOIDS) Justin Timberlake & Britney Spears during Super Bowl XXXVI - Britney Spears & Justin Timberlake Host Super Bowl Fundraiser at Planet Hollywood Times Square at the Planet Hollywood Times Square in New York City, NY. (Photo by Denise Trusc
Justin Timberlake during NBA Hoop It Up Celebrity Tournament at First Union Center in Philadelphia, Pennsylvania, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Justin Timberlake of 'N Sync and Busta Rhymes during The 44th Annual GRAMMY Awards - Clive Davis Pre-GRAMMY Party at Beverly Hills Hotel in Beverly Hills, California, United States. (Photo by L. Cohen/WireImage)
Justin Timberlake, Lisa 'Left Eye' Lopes and Chris Kirkpatrick, photographed during Nsync 'No String Attached' album release party in New York. Lopes was killed in a car crash in the Honduras April 25, 2002. (Photo by Kevin Mazur/WireImage)
Justin Timberlake and Nelly during *NSYNC Challenge for the Children IV - Celebrity Basketball Game at TD Waterhouse Centre in Orlando, Florida, United States. ***Exclusive*** (Photo by James Devaney/WireImage)
Justin Timberlake during The 2002 Teen Choice Awards - Arrivals at The Universal Amphitheatre in Universal City, California, United States. (Photo by SGranitz/WireImage)
Justin Timberlake of NYSNC with mom in the audience attending the 2002 MTV Video Music Awards at Radio City Music Hall in New York City, August 29, 2002. Photo by Frank Micelotta/ImageDirect.
HOLLYWOOD - SEPTEMBER 18: *NSYNC singer Justin Timberlake attends the 3rd Annual Latin Grammy Awards at the Kodak Theatre on September 18, 2002 in Hollywood, California. (Photo by Robert Mora/Getty Images)
Justin Timberlake on 44th street in Times Square on MTV's Spankin New Music Week on TRL in New York City, November 5, 2002. Photo by Frank Micelotta/ImageDirect
Justin Timberlake during 2002 Billboard Music Awards - Arrivals at MGM Grand Arena in Las Vegas, Nevada, United States. (Photo by L. Cohen/WireImage)
Justin Timberlake at the Madison Square Garden in New York City, New York (Photo by Kevin Mazur/WireImage)
Host Sharon Osbourne, Justin Timberlake and her dog Minnie present the Pop/Rock Favorite Band, Duo or Group at the 30th Annual American Music Awards (Photo by M. Caulfield/WireImage)
Sean 'P. Diddy' Combs and Justin Timberlake (Photo by Larry Busacca/WireImage)
Justin Timberlake during Nickelodeon's 16th Annual Kids' Choice Awards 2003 - Arrivals at Barker Hanger in Santa Monica, California, United States. (Photo by Jeffrey Mayer/WireImage)
DUBLIN, IRELAND - MAY 22: Singer Justin Timberlake performs at The Point Theatre May 22, 2003 in Dublin, Ireland. (Photo by Getty Images)
Leno questions an embarrassed Timberlake about rumors that he's dating actress Cameron Diaz (Photo by Paul Drinkwater/WireImage)
Justin Timberlake during Molson Canadian Rocks for Toronto - Press Room at Downsview Park in Toronto, Ontario, Canada. (Photo by Theo Wargo/WireImage)
Eva Mendes Presents Showman of the Year to Justin Timberlake (Photo by KMazur/WireImage)
Justin Timberlake during Justin Timberlake and Mandy Moore Visit MTV's 'TRL' - October 21, 2003 at MTV Studios, Times Square in New York City, New York, United States. (Photo by Theo Wargo/WireImage)
HOUSTON, TX - FEBRUARY 1: Justin Timberlake (right) and Janet Jackson perform during the halftime show at Super Bowl XXXVIII between the New England Patriots and the Carolina Panthers at Reliant Stadium on February 1, 2004 in Houston, Texas. (Photo by Andy Lyons/Getty Images)
LOS ANGELES - FEBRUARY 8: Singer Justin Timberlake poses with his Grammys poses backstage in the Pressroom at the 46th Annual Grammy Awards held on February 8, 2004 at the Staples Center, in Los Angeles, California. (Photo by Frederick M. Brown/Getty Images)
SUNRISE, FL - JULY 25: Justin Timberlake at NSYNC Challenge For The Children Celebrity Basketball Game at Office Depot Center in Sunrise, Florida on July 25, 2004. (Photo by Alexander Tamargo/Getty Images)
Justin Timberlake, presenter during 20th Annual Rock and Roll Hall of Fame Induction Ceremony - Show at Waldorf Astoria in New York City, New York, United States. (Photo by Dimitrios Kambouris/WireImage)
Morgan Freeman and Justin Timberlake during 2005 Toronto Film Festival - 'Edison' Press Conference at Sutton Place in Toronto, Ontario, Canada. (Photo by George Pimentel/WireImage)
Justin Timberlake during Justin Timberlake and Ludacris Visit MTV's 'TRL' - November 2, 2005 at MTV Studios - Times Square in New York City, New York. (Photo by Theo Wargo/WireImage)
PARK CITY - JANUARY 26: Actor Emile Hirsch and singer Justin Timberlake appear on AOL Unscripted at the Meyer Gallery during the Sundance Film Festival January 24, 2006 in Park City, Utah. Their film, 'Alpha Dog' premiered at the Sundance Film Festival 2006. (Photo by Matthew Peyton/Getty Images)
Justin Timberlake at the Sony Pictures in Culver City, California (Photo by Kevin Mazur/WireImage)
Justin Timberlake during 2006 MTV Video Music Awards - Arrivals at Radio City Music Hall in New York City, New York, United States. (Photo by Dimitrios Kambouris/WireImage)
Justin Timberlake (Photo by Kevin Mazur/WireImage)
Hollywood, UNITED STATES: Singer Justin Timberlake performs during the Victoria's Secret Fashion Show in Hollywood, 16 November 2006. AFP PHOTO GABRIEL BOUYS (Photo credit should read GABRIEL BOUYS/AFP/Getty Images)
Justin Timberlake during 64th Annual Golden Globe Awards - Arrivals at Beverly Hilton in Beverly Hills, CA, United States. (Photo by SGranitz/WireImage)
Los Angeles, UNITED STATES: Singer Justin Timberlake and 'My GRAMMY Moment' winner Robyn Troup perform during the 49th Annual Grammy Awards in Los Angeles 11 February 2007. AFP PHOTO/Robyn BECK (Photo credit should read ROBYN BECK/AFP/Getty Images)
Justin Timberlake, host (Photo by Chris Polk/FilmMagic)
Justin Timberlake and Cameron Diaz (Photo by Jon Furniss/WireImage)
NETHERLANDS - JUNE 16: Photo of Justin TIMBERLAKE; performing live onstage (Photo by Rob Verhorst/Redferns)
ABU DHABI, UNITED ARAB EMIRATES - DECEMBER 06: Justin Timberlake performs on stage at the closing night of his FutureSex/LoveShow World Tour in the grounds of Emirates Palace Hotel on December 6, 2007 in Abu Dhabi, United Arab Emirates. (Photo by Dave Hogan/Getty Images)
SANTA MONICA, CA - JUNE 08: Actor/singer Justin Timberlake presents the Lucille Ball Legacy of Laughter Award onstage during the 6th annual 'TV Land Awards' held at Barker Hangar on June 8, 2008 in Santa Monica, California. (Photo by Kevin Winter/Getty Images for TV Land)
(EXCLUSIVE, Premium Rates Apply) NEW YORK - NOVEMBER 13: *Exclusive* (NO ITALY SALES) Justin Timberlake performs inside Keep A Child Alive's 5th annual Black Ball at Hammerstein Ballroom on November 13, 2008 in New York City. (Photo by Kevin Mazur/WireImage)
Singer Justin Timberlake poses in the press room at the 61st Primetime Emmy Awards held at the Nokia Theatre on September 20, 2009 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
NEW YORK - MAY 03: Jessica Biel and Justin Timberlake attends the Costume Institute Gala Benefit to celebrate the opening of the 'American Woman: Fashioning a National Identity' exhibition at The Metropolitan Museum of Art on May 3, 2010 in New York City. (Photo by Kevin Mazur/WireImage)
THE TONIGHT SHOW WITH JAY LENO -- Episode 3897 -- Pictured: Actor/musician Justin Timberlake during an interview on September 20, 2010 -- Photo by: Paul Drinkwater/NBC/NBCU Photo Bank
WEST HOLLYWOOD, CA - FEBRUARY 27: (EXCLUSIVE ACCESS SPECIAL RATES APPLY; NO NORTH AMERICAN ON-AIR BROADCAST UNTIL MARCH 3, 2011) Jessica Biel and Justin Timberlake attend the 2011 Vanity Fair Oscar Party Hosted by Graydon Carter at the Sunset Tower Hotel on February 27, 2011 in West Hollywood, California. (Photo by Kevin Mazur/VF11/WireImage)
WESTWOOD, CA - OCTOBER 20: Actor/Singer Justin Timberlake arrives at the Premiere of Regency Enterprises' 'In Time' at the Regency Village Theater on October 20, 2011 in Westwood, California. (Photo by Frazer Harrison/Getty Images)
NEW YORK, NY - MAY 07: Jessica Biel and Justin Timberlake attend the 'Schiaparelli And Prada: Impossible Conversations' Costume Institute Gala at the Metropolitan Museum of Art on May 7, 2012 in New York City. (Photo by Kevin Mazur/WireImage)
NEW ORLEANS, LA - FEBRUARY 02: Justin Timberlake performs at DIRECTV Super Saturday Night Featuring Special Guest Justin Timberlake & Co-Hosted By Mark Cuban's AXS TV on February 2, 2013 in New Orleans, Louisiana. (Photo by Christopher Polk/Getty Images for DirecTV)
LOS ANGELES, CA - FEBRUARY 10: Singer Justin Timberlake attends the 55th Annual GRAMMY Awards at STAPLES Center on February 10, 2013 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
LONDON, ENGLAND - FEBRUARY 20: Justin Timberlake performs on stage during the Brit Awards 2013 at the 02 Arena on February 20, 2013 in London, England. (Photo by Matt Kent/Getty Images)
CANNES, FRANCE - MAY 19: Actor Justin Timberlake attends the 'Inside Llewyn Davis' photocall during the 66th Annual Cannes Film Festival at the Palais des Festivals on May 19, 2013 in Cannes, France. (Photo by Andreas Rentz/Getty Images)
US actor and singer Justin Timberlake smiles on May 20, 2013 as he takes part in the show 'Le Grand Journal' on the set of the French TV Canal+, on the sidelines the 66th Cannes film festival in Cannes. Cannes, one of the world's top film festivals, opened on May 15 and will climax on May 26 with awards selected by a jury headed this year by Hollywood legend Steven Spielberg. AFP PHOTO / LOIC VENANCE (Photo credit should read LOIC VENANCE/AFP/Getty Images)
NEW YORK, NY - AUGUST 25: Musician Justin Timberlake performs onstage during the 2013 MTV Video Music Awards at the Barclays Center on August 25, 2013 in the Brooklyn borough of New York City. (Photo by Neilson Barnard/Getty Images for MTV)
RIO DE JANEIRO, BRAZIL - SEPTEMBER 15: Justin Timberlake performs on stage during a concert in the Rock in Rio Festival on September 15, 2013 in Rio de Janeiro, Brazil. (Photo by Buda Mendes/Getty Images)
LOS ANGELES, CA - NOVEMBER 24: Recording artist Justin Timberlake, winner of Favorite Male Artist - Pop/Rock, Favorite Male Artist - Soul/R&B, and Favorite Album - Soul/R&B for 'The 20/20 Experience,' poses in the press room at the 2013 American Music Awards at Nokia Theatre L.A. Live on November 24, 2013 in Los Angeles, California. (Photo by Gregg DeGuire/WireImage)
LONDON, ENGLAND - APRIL 01: Justin Timberlake performs on his 20/20 Experience World Tour at The O2 Arena on April 1, 2014 in London, England. (Photo by Dave J Hogan/Getty Images)
THE TONIGHT SHOW STARRING JIMMY FALLON -- Episode 0325 -- Pictured: (l-r) Singer Justin Timberlake during an interview with host Jimmy Fallon on September 9, 2015 -- (Photo by: Douglas Gorenstein/NBC/NBCU Photo Bank via Getty Images)
BEVERLY HILLS, CA - OCTOBER 23: Jessica Biel and Justin Timberlake arrives at the 2015 GLSEN Respect Awards at the Beverly Wilshire Four Seasons Hotel on October 23, 2015 in Beverly Hills, California. (Photo by Steve Granitz/WireImage)
BEVERLY HILLS, CA - FEBRUARY 28: Recording artist Justin Timberlake attends the 2016 Vanity Fair Oscar Party Hosted By Graydon Carter at the Wallis Annenberg Center for the Performing Arts on February 28, 2016 in Beverly Hills, California. (Photo by Pascal Le Segretain/Getty Images)
INGLEWOOD, CALIFORNIA - APRIL 03: Recording artists Justin Timberlake (L) and Taylor Swift attends the iHeartRadio Music Awards which broadcasted live on TBS, TNT, AND TRUTV from The Forum on April 3, 2016 in Inglewood, California. (Photo by Frazer Harrison/Getty Images for iHeartRadio / Turner)
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Right now, in early February, as awards season reaches maximum velocity, Timberlake once again is in the news — his song "Can't Stop the Feeling!" has been nominated for an Oscar, the singer's first. He wrote the bouncy disco tune for DreamWorks Animation's November hit Trolls, in which he voices a gloomy troll named Branch who befriends Anna Kendrick's more upbeat Princess Poppy (it has grossed $339 million worldwide). But the song also was created as a gift to his (and wife Jessica Biel's) 2-year-old son, Silas. "I'd never have written it if it weren't for him," he says. Either way, the earworm took off on the charts to become Timberlake's first No. 1 single in 10 years, selling 2.4 million downloads (and streaming nearly 700 million times). For the few who impossibly haven't yet heard the number, there's an excellent chance he'll be singing it at the Oscars — "it's being negotiated," is all he'll say — though don't expect to see Timberlake at the Feb. 12 Grammys, which snubbed the tune for the big prizes and nominated it only for best song written for a visual media. Timberlake will be playing golf at Pebble Beach that weekend.

There aren't a lot of boy band singers who mature into grown-up pop stars. And there aren't a lot of pop singers who cross over to become bona fide movie stars. And there's pretty much only one who has come close to doing both. Timberlake has toured with Christina Aguilera and acted for David Fincher (The Social Network). He has sung duets with Madonna and starred in a Coen brothers film (Inside Llewyn Davis). He's been a Mouseketeer, a teen heartthrob, Cameron Diaz's love object (both on and off the screen), Jimmy Fallon's best friend (and best comedy partner), a political activist (at least he threw a fundraiser for Hillary Clinton) and very soon might well become an Oscar winner. The question now, of course — the one Timberlake says he's been asking himself a lot lately — is what does he most want to be next?

•••

Here are some ofTimberlake's "faint images" of his pre-famous boyhood: learning to sing in the church in Shelby Forest, Tenn., where his father was the choir director; his parents divorcing when he was in kindergarten and moving to Memphis with his mom (who remarried a banker); playing basketball and taking voice lessons in grade school.

Miller Mobley

Lately, since the birth of his son, Timberlake's been rummaging more and more in those memories — and how, when he was 10, his childhood took its abrupt swerve toward the unusual. "You go through your life with your own traumas, big and small, and think, 'It's not that bad, I have a lot to be thankful for, my parents did the best they could,' " he says. "But then you have a child of your own, and suddenly it opens all the floodgates, and you're like, 'No, no, no! That childhood trauma really did f— me up!' "

When he was in fourth grade, he heard about an open call at a Memphis mall where talent scouts were looking for contestants for Ed McMahon's Star Search ("the original American Idol," Timberlake calls it). He sang his heart out and got flown with his mom to Orlando for a slot on the show. He ended up losing — he blames the Garth Brooks song he was coaxed by the producers into singing — but he was hooked. A year later, when 11-year-old Justin found out that Disney Channel was casting The New Mickey Mouse Club in Orlando, he persuaded his mom to take him back to Florida to audition. This time, he made the cut, which is how he ended up being castmates with future girlfriend Spears, Keri Russell and future tourmate Aguilera and bunking with 11-year-old Ryan Gosling, who spent a season of the show living with Timberlake and his mom ("We aren't the closest of friends, for whatever reason," says Timberlake nonchalantly when asked whether he has stayed in touch with the La La Land star) in what turned out to be the greatest incubator of preteen talent in Mouseketeer history.

"We were at the age when you just soak in everything," says Timberlake. "We were taking acting classes, music classes, dance classes. We were learning how coverage and editing and cinematography work. And being put in front of a live audience, learning how to engage the crowd to get a laugh. Honestly, it was like SNL for children."

Timberlake's smooth moves during the show's five seasons caught the eye of famed music producer (and, later, convicted embezzler) Lou Pearlman, who had just made a fortune launching Backstreet Boys and was seeking to replicate that feat. He offered 15-year-old Timberlake a spot in his latest boy band and, in 1996, NSYNC released its debut album. It was an overnight smash in Europe (especially Germany), and within a couple years the group was topping the charts in America as well with bubblegum hits like "I Want You Back" and "Tearin' Up My Heart." Before long, NSYNC was performing at the Super Bowl, the Olympics and the Oscars as well as recording tracks with such music legends as Elton John, Stevie Wonder and Michael Jackson. At one point during the late 1990s — around the time bandmembers started suing Pearlman for stealing from them (he died in 2016 in prison) — the group was selling nearly 2.5 million albums a week, eclipsing even The Beatles.

Technically, NSYNC never officially broke up; they announced a "hiatus" in 2002 and have not appeared together since. "We were on a stadium tour, and I just felt like the whole thing was too big," says Timberlake, explaining why he decided to bail. "It started as a fun snowball fight that was becoming an avalanche. And, also, I was growing out of it. I felt like I cared more about the music than some of the other people in the group. And I felt like I had other music I wanted to make and that I needed to follow my heart."

Timberlake followed his heart in public for the first time at the 2002 MTV Video Music Awards, performing his debut solo single, "Like I Love You." The song hit No. 11 on the Billboard Hot 100 chart, and his debut solo album, Justified, went on to sell 3 million copies, but what was really important about that VMA show was that it marked the start of one of the great bromances of recent pop culture history.

Miller Mobley

"I was hosting by myself for the first time, and Justin was performing by himself for the first time, so we really bonded that night," remembers Fallon, who was moonlighting from his job on Saturday Night Live to emcee the event. "Our dressing rooms were connected, and we were both pacing, trying to calm each other down. 'You're going to be great,' 'No, you're going to be great.' And we've just been pals ever since."

More than pals, they became a hugely popular comedy duo. When Timberlake hosted SNL for the first time in 2003, he and Fallon killed it with their "Barry Gibb Talk Show" skit, beginning a partnership with the show that would have Timberlake returning five more times as host (winning three Emmys for his appearances) and many other times for cameos (like that "Dick in a Box" digital short he made with Lonely Island's Andy Samberg, still among the most downloaded bits in Saturday Night Live history).

Aside from the junior sketch comedy he'd done on The New Mickey Mouse Club, Timberlake had acted only once, in a 2000 Disney TV movie called Model Behavior, playing a male fashion model who falls for a waitress (much eye-rolling at the mention of the title). But after his appearances on SNL, acting offers started falling into his lap. Nick Cassavetes cast him for a small role in his crime drama Alpha Dog, while Hustle & Flow director Craig Brewer put him in Black Snake Moan with Samuel L. Jackson. "How come I cast him? I saw him on Saturday Night Live!" says director Will Gluck, who hired Timberlake to star with Mila Kunis in the romantic comedy Friends With Benefits. "On SNL, he was so funny and natural and likable and encapsulated so many different characters. I just knew this guy was really good."

It's not known why exactly David Fincher became interested in Timberlake — maybe he's a fan of "Dick in a Box," too — but the Oscar-nominated filmmaker asked the singer to try out for the role of Napster founder Sean Parker in 2010's Facebook drama The Social Network. "I went in as the character," recalls Timberlake of his audition with Fincher and writer Aaron Sorkin that ultimately won him the part, his first dramatic role in a major, high-profile production. Timberlake's performance in the film caught a lot of folks in Hollywood by surprise — "From the moment he comes onscreen, he just claims it," gushes Jonathan Demme, who last year directed the Netflix concert film Justin Timberlake and the Tennessee Boys — and there even was talk of a best supporting actor Oscar. The nom didn't happen, but the film nonetheless widened the singer's acting options dramatically, helping him land leading parts in big films (like Bad Teacher, opposite ex-girlfriend Diaz) and prestige indie projects (like Joel and Ethan Coen's folk music drama Inside Llewyn Davis). As Timberlake succinctly puts it, "There are two parts to my acting career: before The Social Network and after."

Of course, for serious thespians, the ultimate status symbol remains a part in a Woody Allen movie, even if these days that honor is mixed with moral complications (Timberlake sidesteps the ethics: "I chose to not get into it — I really don't dive into any of that stuff with anybody"). Like all of Allen's productions, this one is shrouded in secrecy, and Timberlake is keeping his lips sealed. Although judging from photos leaked in the fall of Timberlake on the set in a lifeguard chair wearing a 1950s-style two-piece swimsuit, Coney Island may figure into the plot. In any case, for Timberlake, it's yet another step up a ladder he never imagined he'd find himself climbing. "I can't really say that doing a Woody Allen movie was ever on my bucket list," he says, "because I never even thought that doing a Woody Allen movie might be a possibility."

•••

At this juncture of his career, Timberlake still is more pop star than movie star. He doesn't have his next film lined up after the Allen project — which wrapped in November — but he sure knows what his next album will be (even if it doesn't yet have a release date). He's been working on it for months, collaborating with Pharrell, Timothy Mosley (otherwise known as Timbaland) and producer Max Martin (who helped write "Can't Stop the Feeling!" and two of the other four original songs Timberlake penned for the soundtrack, which Timberlake also executive produced). In fact, just the other night, he was holed up in the studio, "caught up in a creative tornado," until three in the morning. "It sounds more like where I've come from than any other music I've ever made," he describes what he's been working on. "It's Memphis. It's Southern American music. But I want to make it sound modern — at least that's the idea right now."

Until now, Timberlake has toggled more or less at will between the worlds of music and film, occasionally melding both (he scored his wife's next movie, The Book of Love). After his second album, FutureSex/LoveSounds, went platinum in 2007, he put singing on hold and spent a few years focusing on his acting. Then, in 2013, he took a break from acting to resume singing, launching a two-year worldwide tour following the release of his third album, 20/20 (at $231 million, his highest-grossing tour to date). "I want to do both things," he says. "I really do idolize the golden era of Hollywood, when actors were required to sing and move. But I'm just following my gut in the decisions that I make about what I'm going to do next. I'm mostly just glad this is all working out because I really can't do anything else. I'm not gifted at anything else."

Miller Mobley

Lately, though, Timberlake's gut has been acting up, leaving him unsure whether he'll be spending his next few years more on movie sets or on tour buses. Part of it may just be age — he's not 16 anymore. "Going on tour is a circus," he says. "You set up the tents, you play the show, you tear the tents down and go on to the next place. It's like Groundhog Day. After the 125th show, you feel debilitated." Another part of his confusion may be post-election jitters: He and his wife were big Clinton supporters — they held their fundraiser at their L.A. home last summer (filling in for Leonardo DiCaprio after he canceled his) — and Timberlake, whose musical brand always has been exuberantly upbeat, still is trying to adjust his cultural antennae to the new world zeitgeist. "Everything feels divisive to me right now," he says. "Everything." Probably the biggest reason he's having difficulty deciding which way to steer his career, however, is the 2-year-old who inspired that disco song that put Timberlake back on top of the charts last year. "Watching him jump around to 'Can't Stop the Feeling!' starting to learn words because of that song — it's the best thing in the world," he says with a giant grin.

Like every new dad, Timberlake is struggling to make adjustments to the work-life balance. "At first, it broke me down," he admits. "Those first eight months felt like those old [Ed Sullivan] shows where people are balancing spinning plates on poles — except if you drop one, they die." Of course, kids also have a way of making parents re-evaluate their own past, of rethinking their own choices and wondering whether their children might find a better, easier, healthier way. "Would I want my child to follow my path?" contemplates Timberlake, pausing for a long swig of beer. "You know, I haven't been able to answer that question in my mind. If he wanted it bad enough, I suppose I could teach him a lot about what not to do."

Miller Mobley

This story first appeared in the Feb. 17 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.


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