Crooked Smile

In an interview for Power 106 on June 13, 2013, Cole explained that the song's recording process was his longest and most strenuous because of the potential he saw. He thought TLC would be ideal after coming up with the hook, finding collaborating with them to be "crazy" and "far-fetched".[2] Cole was a fan of TLC's musicianship on the likes of "Unpretty" (1999) and "Waterfalls" (1995); he worked with the members in separate studios, meeting T-Boz in Los Angeles and then flying to Atlanta for Chilli. Chilli danced to his songs, an experience he highly appreciated. After having achieved success, Cole felt insistent on keeping his "crooked smile".[2] Two months after Cole's interview, T-Boz revealed that he contacted TLC. He understood that the song's message is what the group stand for and lauded Cole as an artist, gaining respect for him due to his deep lyricism and production.[3] In his six-minute MTV documentary "Life & Rhymes: J. Cole - Crooked Smile" in October 2012, Cole detailed that he re-wrote the song's verses repeatedly to make it have a broader appeal than rap, rather than a song "about his smile or his teeth".[4] The song was set out as a theme song of the album's second half, which represents seeing the light mentally.[4]

At a concert for Footaction in Hollywood on October 19, 2012, Cole previewed "Crooked Smile" and a track titled "Man on Fire", although no release on a project was known initially.[5] The former was later released as a single for Born Sinner in June 2013, a day after Cole performed the lead single "Power Trip" at Summer Jam XX.[6] The song also premiered on SoundCloud.[7] On January 28, 2014, the original version of the song was released on Dreamville Records' compilation Revenge of the Dreamers, which celebrated Cole's partnership with the label.[8]

J. Cole raps the verses, and TLC sings the chorus. Throughout the verses, J. Cole talks about the women who are insecure about what they look like, and tells them they look good. He also talks about the things people do to make themselves look good, when inside they want to be the same person they were, even before doing all those things. In the chorus, TLC sings about the people who kept them down, but also break free from. At the end of the song, the choir hums the chorus.

After Cole and TLC had teased the music video for over a month, on September 18, 2013 the video was released.[9] TLC does not appear in the video with J. Cole but their verses are featured. It is dedicated to Aiyana Stanley-Jones.

Cole first performed "Crooked Smile" at the end of his set for Footaction's "Own the Stage" event in W Hotels' Hollywood location on October 19, 2012.[5][10] He performed the song at a private show in New York City (NYC) on June 4, 2013.[11] On June 12, Cole delivered a rendition of it with backing from live instrumentation on Power 106's series 'Backstage Breakfast'.[12] He performed the song for Sirius XM on June 28, 2013, introducing it by focusing on embracing yourself despite people finding flaws.[13] At the 2013 BET Awards, Cole performed the song solo as he sat on a stool and Born Sinner's cover art flashed in the background.[14][15] He performed it with backing band the Roots at the 2013 Philly 4th of July Jam, rocking a Toledo Mud Hens baseball jersey and camouflage shorts. Cole sat on a stool for an introduction, discussing television images and offering that he is frequently reminded "that my eyebrows is real thick and my smile ain't perfect".[16] Cole served as a musical guest on TBS' Conan on August 13, 2013, performing the song. He was flanked by a live band and two female back-up singers, who sang TLC's portion.[17][18][19]

Cole performed the song with TLC at the 2013 iHeartRadio Music Festival in Las Vegas, standing as their first joint performance and the group came out during his introduction to cheers from the crowd. TLC wore futuristic black costumes that resembled the group in their 1999 video for "No Scrubs", interacting with the audience as they danced and Cole rapped with a smile.[1] Cole performed the song at the Ed Sullivan Theater in Manhattan, NY for the Late Show with David Letterman on November 5, 2013, marking his first appearance on the show since 2011.[20][21] He was supported by a string quartet, a DJ, a backing band, and a pair of female singers that delivered TLC's part, increasing from his line-up on Conan.[20][22][23] Cole wore a leather jacket and a hat facing backwards for the performance, which David Letterman called "Fantastic!" as he blew a kiss to the line-up.[20][23] On August 4, 2015, Cole performed the song for a concert at Madison Square Garden in NYC on his Forest Hills Drive tour.[24] During his appearance on Day 2 of the 2016 Billboard Hot 100 Festival at Nikon at Jones Beach Theater in Wantagh, NY, Cole performed it for his encore.[25]

Rolling Stone ranked the song at number 37 on their list of the 100 Best Songs of 2013.[26] The song was nominated for The Ashford and Simpson Songwriter’s Award at the 2013 Soul Train Music Awards.[27] The music video was nominated for a 2014 MTV Video Music Award for Best Video With A Social Message.[28]