Songfacts®:

• This piano-driven banger was released as the second official single from J. Cole's Born Sinner album. The ode to self-love, which was produced by J. Cole himself, finds him counselling women to embrace their inner beauty and what God has already created with his paint brush. "It's a very empowering song," he said of the track at a London playback of the record. "I don't have that Colgate smile and people keep reminding me about it. People are always looking to criticize you and I started to feel self-conscious about it - it takes you back to high school."
• The song features Tionne "T-Boz" Watkins and Rozonda "Chilli" Thomas from the American girl group TLC singing on the track's hook. Originally a trio, along with the late Lisa "Left Eye" Lopes, the R&B threesome recorded a string of hits in the 1990s, including the Hot 100 #1s "Creep," "Waterfalls," "No Scrubs" and "Unpretty." According to Cole, TLC were one of his favorite groups when he was growing up.
• Though Cole really does have a crooked smile, he told Hartford, Connecticut radio station Hot 93.7 that the tune's message is bigger than his own imperfections. "The song is bigger than just my thing, it's about everybody's thing," he said. "Society tries to tell you there's something about you that makes you inferior to the images they're trying to put out there. [The song] is really me embracing my [imperfections] and trying to get other people to embrace theirs."
• The original version of this song was three verses that Cole rapped over a Tupac beat. It started coming to life at a private show in L.A., where during the sound check Cole and his band decided to add a little jam session for the fans. The keyboard player played to a beat that Cole had made with a Jennifer Hudson sample and the rapper realized straight away that it completely fitted with the first verse on "Crooked Smile". Cole's right hand man Ibrahim "IB" Hamad recalled to Vibe magazine: "I've never been a part of a song that was worked on for as long as this one. it was incredible to see the transformation. Elite came in and co-produced the record with him and they really took their time on this record. I remember everybody watching a lot of Quincy Jones interviews and documentaries around that time. We all knew this record was special and it was treated that way by everyone involved.
  
  "Once the hook was added," he continued, "Cole already had in his mind he wanted to work with TLC. It had a very 'Unpretty' feel to it. The vibe of the record and the message was perfect for them."
• The Born Sinner album is split into two halves. Cole explained to Hartford, Connecticut radio station Hot 93.7: "The first half is depressed and like hell. The second half is like heaven. 'Crooked Smile' is the theme song for the second half of the album. It is like making it out of the depression and celebrating it."
• The song was TLC's first single to reach the Top 40 of the Hot 100 since "Girl Talk" peaked at #28 in 2002.
• The Sheldon Candis directed music video finds Cole portraying a drug dealer. The clip is dedicated to the memory of 7-year-old Aiyana Stanley-Jones, who was shot and killed in 2010 during a raid on her family's Detroit home. The visual sticks close to the narrative that led to the tragic death of Aiyana. "For Aiyana Stanley-Jones," the video's message reads. "And please reconsider your war on drugs."
• Cole revealed in the MTV documentary Life & Rhymes: J. Cole – Crooked Smile the struggles he went through when crafting this tune. "I wanted it to be bigger than rap. I wanted it to be universal," he said. "So I kept trying to write these verses that would elevate the song and make it appeal to the world and not a J. Cole song about his smile or his teeth."
• The hook was written by Polly A, a singer-songwriter formerly known as Meleni Smith. "He starts playing 'Crooked Smile,' he has the verses and everything," she recalled to Billboard magazine. "I'm like, 'This is all me. I got this!' [Laughs]. The first thing I sang was what was the hook. [I] literally wrote it in 30 minutes."
  
  Polly A's other writing credits include Alicia Keys' "Love is My Disease" and "Happy" from the 2005 Hitch movie soundtrack.