An accompanying music video was released in September 2013, which Sheldon Candis directed after Roc Nation phoned him and he met Cole at the Los Angeles International Airport.

The music video depicts Cole as a marijuana dealer, and he celebrates his sister's birthday with their family until the Drug Enforcement Administration raid the house and kill her.

[1] 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.

[3] In an interview for Fuse, Cole compared the song to deceased rapper 2Pac's "Keep Ya Head Up" (1993) and explained its empowerment message, encouraging people to embrace their flaws and "not to be so caught up in the little things".

[5] 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.

[10][11][12][13] The song features a jazz groove that relies on piano chords and contains a sample of the 2011 single "No One Gonna Love You", performed by singer and actress Jennifer Hudson.

In a review of the song for MTV, Jenna Hally Rubenstein highlighted Cole's lyricism and TLC's appearance that she heavily compared to "Unpretty", as well as praising the piano instrumentation.

[7] AllMusic's David Jeffries said that with TLC's appearance, the song is a "genuine, mature step in the right direction" for Cole and will easily reach "vintage age".

[14] In Slant Magazine, Ted Scheinman noted the song's emotional appeal and that Cole "serves as [a] motivational speaker", consoling a woman for her different aspects and offering his talent of "turning heavy ballad material into a club-banging dance track".

[23] Jesal 'Jay Soul' Padania from RapReviews envisioned the "catchy and heartfelt TLC-featuring hit" receiving airplay with a large budget video and thought it initially seems insincere, yet "the message is worth the saccharin".

[26] HipHopDX's Jesse Fairfax believed that the song does not fit the album's "prevalent darker tone" outside of any commercial appeal, while ZCamp of Tiny Mix Tapes criticized the "nondescript piano" as bland and boring.

[29] Rolling Stone ranked the song as the year's 37th best; the staff wrote that the piano chords resemble fellow rapper Kanye West's 2004 debut The College Dropout and Cole tackles insecurities, providing "lush soul rap that's uplifting but never boring".

[33] Candis then approached Cole when he was at the Los Angeles International Airport catching a red-eye to New York (NY), introducing himself as he held his MacBook and offered to show him the film's trailer.

[34] It includes a tribute to Dominika Jones' deceased 7-year-old daughter Aiyana Mo'Nay Stanley-Jones, who was killed in a police raid at her Detroit home in 2010, and a message for the US government's war on drugs.

[33] Chairman of Justice for the Stanley-Jones' committee Roland Lawrence issued a statement applauding Cole's thoughtfulness, recognizing that the video "hopefully will call us all on the table as it pertains to injustice in America" and everywhere else.

[37] The music video begins with interspersed shots of Cole and a Drug Enforcement Administration (DEA) agent going through similar morning routines, first brushing their teeth.

[36] Cole is arrested by the DEA agent and watches as his sister is accidentally shot and killed upon being found, while he reflects on the preceding day's events of the family.

[53][54] 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".

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.

[59][60] 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.