On Thursday Nov. 5, Smith debuted his emotional rendition of Winehouse's "Love Is a Losing Game" on BBC Radio's Annie Mac show.
"Sometimes people forget my age, I think. I was 11-years-old when 'Frank' came out and that album has really shaped me as an artist and my views on music and my relationship with music, lyrically...Just her rawness on such beautiful chords."
Sam Smith, BBC Radio
"That lyric 'love is a losing game,' is possibly one of the most relatable lyrics I've ever heard. So, I just pretended all those things she's talking about happened to me; which they probably have, in terms of love and losing out."
Sam Smith, BBC Radio
Sam Smith's cover of "Love is a Losing Game" is available on the deluxe version of his album, along with many surprises you won't find in the original.
See some of our favorite Sam Smith photos here:
Sam Smith's latest Amy Winehouse cover will give you goosebumps
LOS ANGELES, CA - FEBRUARY 15: Sam Smith attends the 58th GRAMMY Awards at Staples Center February 15, 2016 in Los Angeles, California. (Photo by Sammy Smith/WireImage)
LOS ANGELES, CA - FEBRUARY 10: Sam Smith arrives at the SAINT LAURENT At The Palladium at Hollywood Palladium on February 10, 2016 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
BEVERLY HILLS, CA - FEBRUARY 08: Singers/songwriters Jimmy Napes (L) and Sam Smith attend the 88th Annual Academy Awards nominee luncheon on February 8, 2016 in Beverly Hills, California. (Photo by Kevork Djansezian/Getty Images)
Jimmy Napes, left, and Sam Smith pose in the press room with the award for best original song in a motion picture for âWritingâs on the Wallâ from âSpectre" at the 73rd annual Golden Globe Awards on Sunday, Jan. 10, 2016, at the Beverly Hilton Hotel in Beverly Hills, Calif. (Photo by Jordan Strauss/Invision/AP)
Sam Smith arrives at the 73rd annual Golden Globe Awards on Sunday, Jan. 10, 2016, at the Beverly Hilton Hotel in Beverly Hills, Calif. (Photo by Jordan Strauss/Invision/AP)
IMAGE DISTRIBUTED FOR CITY OF HOPE - Sam Smith performs at the City of Hopeâs Spirit of Life Gala, honoring UMG's Chairman and CEO Lucian Grainge at the Santa Monica Civic on Thursday, Nov. 5, 2015. (Photo by Matt Sayles/Invision for City of Hope/AP Images)
LONDON, UNITED KINGDOM - JUNE 21: In this handout image supplied by Ray-Ban, Sam Smith poses at the Ray-Ban Rooms at Barclaycard Presents British Summer Time in Hyde Park on June 21, 2015 in London, United Kingdom. (Photo by Ray-Ban via Getty Images)
Singer Sam Smith is spotted at LAX Airport in Los Angeles, Ca after canceling tour dates to seek medical treatment
Picture by: Quarterflash/Vantage News
5 May 2015.
Picture by: Quarterflash/Vantage News
5 May 2015.
Photo by: KGC-138/STAR MAX/IPx 3/14/15 Sam Smith at the Alexander McQueen: Savage Beauty Exhibition VIP Private Viewing at the Victoria and Albert Museum. (London, England, UK)
LAS VEGAS, NV - MAY 17: Recording artist Sam Smith accepts the Top Radio Songs Artist award via video onstage during the 2015 Billboard Music Awards at MGM Grand Garden Arena on May 17, 2015 in Las Vegas, Nevada. (Photo by Ethan Miller/Getty Images)
LOS ANGELES, CA - MARCH 29: Singer Sam Smith (via video) performs during the 2015 iHeartRadio Music Awards which broadcasted live on NBC from The Shrine Auditorium on March 29, 2015 in Los Angeles, California. (Photo by Kevin Winter/Getty Images for iHeartMedia)
MUNICH, GERMANY - MARCH 04: Singer Sam Smith (R) and the CEO of Universal Music Deutschland, Frank Briegmann, pose for a picture after a concert at Zenith on March 4, 2015 in Munich, Germany. (Photo by Dominik Bindl/Getty Images for Universal Music)
British singer-songwriter Sam Smith poses with his British breakthrough act award and his BRITs global success award at the BRIT Awards 2015 in London on February 25, 2015. AFP PHOTO / LEON NEAL
RESTRICTED TO EDITORIAL USE, TO ILLUSTRATE THE EVENT AS SPECIFIED IN THE CAPTION, NO USE IN PUBLICATION DEVOTED TO SINGLE PERFORMER (Photo credit should read LEON NEAL/AFP/Getty Images)
LONDON, ENGLAND - FEBRUARY 23: Sam Smith attends the Burberry Prorsum AW 2015 arrivals during London Fashion Week at Kensington Gardens on February 23, 2015 in London, England. (Photo by Gareth Cattermole/Getty Images for Burberry)
LOS ANGELES, CA - FEBRUARY 08: Singer Sam Smith attends the Universal Music Group 2015 Post GRAMMY Party at The Theatre Ace Hotel Downtown LA on February 8, 2015 in Los Angeles, California. (Photo by Frederick M. Brown/Getty Images)
LOS ANGELES, CA - FEBRUARY 08: Singer Sam Smith (R) and songwriter James Napier accept the Song of the Year award for 'Stay With Me' onstage during The 57th Annual GRAMMY Awards at the at the STAPLES Center on February 8, 2015 in Los Angeles, California. (Photo by Kevork Djansezian/Getty Images)
NEW YORK, NY - JANUARY 15: Sam Smith performs at Madison Square Garden on January 15, 2015 in New York City. (Photo by Theo Wargo/Getty Images)
NEW YORK, NY - DECEMBER 12: Sam Smith performs onstage during iHeartRadio Jingle Ball 2014, hosted by Z100 New York and presented by Goldfish Puffs at Madison Square Garden on December 12, 2014 in New York City. (Photo by Mike Coppola/Getty Images for iHeartMedia)
NEW YORK, NY - JUNE 16: Sam Smith at Good Morning America to promote his debut CD, The Lonely Hour on June 16, 2014 in New York City. Credit: RW/MediaPunch/IPX
LOS ANGELES, CA - AUGUST 25: Singer Sam Smith performs at the Red Bull Sound Space at 97.1 AMP Radio on August 25, 2014 in Los Angeles, California. (Photo by Chelsea Lauren/Getty Images for AMP Radio)
NEW YORK, NY - JUNE 17: Sam Smith performs at The Apollo Theater on June 17, 2014 in New York City. (Photo by Theo Wargo/Getty Images for Capitol Records)
Sam Smith performs at The 2014 mtvU Woodie Awards and Festival at the 2014 SXSW Music, Film + Interactive Festival, on Thursday, March 13, 2014 in Austin, Texas. (Photo by John Davisson/Invision/AP)
NEW YORK, NY - JUNE 17: EXCLUSIVE COVERAGE/SPECIAL RATES APPLY Sam Smith visits 'The Elvis Duran Z100 Morning Show' at Z100 Studio on June 17, 2014 in New York City. (Photo by Rob Kim/Getty Images)
LONDON, ENGLAND - FEBRUARY 19: Sam Smith attends The BRIT Awards 2014 at 02 Arena on February 19, 2014 in London, England. (Photo by Anthony Harvey/Getty Images)
INDIO, CA - APRIL 14: Musician Sam Smith performs onstage with Disclosure during day 3 of the 2013 Coachella Valley Music & Arts Festival at the Empire Polo Club on April 14, 2013 in Indio, California. (Photo by Karl Walter/Getty Images for Coachella)
Sam Smith arrives for the Capital FM Summertime Ball, Wembley Stadium, London, Sunday, June. 9, 2013. (Photo by Jonathan Short/Invision/AP)
ATLANTA, GA - SEPTEMBER 19: Sam Smith performs at Music Midtown at Piedmont Park on September 19, 2015 in Atlanta, Georgia. (Photo by Chris McKay/Getty Images for Live Nation)