Justin Timberlake + Jay Leno Talk 20/20, President Obama, and 'N Sync

Lenny Kravitz, Grace Jones, Lauryn Hill, Lion Babe, Thundercat, SZA & More Rock The Afropunk Festival 2015 in Brooklyn, NY.

Justin Timberlake stopped by The Tonight Show With Jay Leno last night with what he describes as an "antibiotic protozone cocktail" helping him through the interview. Timberlake was ill during his appearance and explained to Leno that he routinely performs despite needing a trash can by the stage for whenever he needed to "release the demons." He then went on to discuss gambling in Las Vegas where he once won $10,000 from a five hour game of blackjack and then lost everything in a five minute game of craps. Leno tried getting him to reveal his largest winnings but he, being the Southern gentleman that he is, refused to talk about earnings on television. However, when asked about his recent stint at the White House, Timberlake was eager to talk about meeting the President:

"He's the coolest guy ever. He had some meeting out of state and he showed up on the Air Force One Helicopter and, you know, I felt weird. I was in his house where he lives and he's not there...He shows up in the helicopter and when the helicopter lands, the thing rolls out and he gets off and you got like a hundred people, everybody - the camera operators, the producers, everybody who was rehearsing - and we all stopped and watched President Obama. He strut off the thing and it was dead silent. Then I looked at everybody and I said, " uh daddy's home."

Along with getting to sing with Obama at the White House celebration of Memphis Soul- Timberlake got him to sing along to "Sittin On The Dock Of The Bay"- Timberlake also had the opportunity to sing with 'N Sync. In what he refers to as  "the worst kept secret of the VMAs", after ten years, the boy band finally got back together to perform a quick (lasting a little over a minute) medley of their greatest hits - "we were all laughing at the fact that people still cared." The performance landed towards the end of Timberlake's much longer solo performance of tracks off his last album, The 20/20 Experience. In the interview, Timberlake explained why the album was divided into two parts:

"I took a month out last year and recorded a ton of music and I called it the 20/20 Experience because I narrowed it down to about 20 songs. Now in hindsight I wish I had a more creative reason for the 20/20 Experience. It was always trying to figure out - see to me it's a double album but then we thought it could be really interesting to have a staggered release where half the record is out for the summer and half the record out for the winter."

The sequel - The 20/20 Experience (2 of 2) - will be released September 30. Pre-order now via iTunes.