"He Wasn't Man Enough" is a dance inspired song, which features more mainstream pop music with strong R&B influences. All instruments were played by Darkchild and the background vocals were sung by Toni Braxton, Nora Payne, Charlotte Gibson and Darkchild. The song's vocal range starts with a D#4 chord to a C#6 chord in a chord of G Major. Popmatters praised Braxton for singing a non-ballad pop song, saying "the track seems to be an attempt to make some headway within the lucrative urban R&B market." The song's length is a total of four minutes and twenty-one seconds at a moderately slow, yet steady pace. The song earned Braxton her sixth Grammy Award for Best Female R&B Vocal Performance in 2001. According to Billboard.com, this song is her last Top 10 appearance on the Billboard Hot 100 to date.
"He Wasn't Man Enough" had received extremely positive reception from contemporary music critics. Stephen Thomas Erlewine from Allmusic had highlighted the track as an album highlight, which along with "Gimme Some" was a "skimmering beat". David Browne from Entertainment Weekly gave it a positive review, certificating it with a B rating. He said "From producer Rodney Jerkins' cushiony pulse to its premise (one woman warning another about her ex-beau), the amenable single "He Wasn't Man Enough" sounds mightily familiar. But it's still no "Scrubs", largely thanks to Braxton's husky, mumbly delivery."NME gave it a positive review, saying that for the track, "Braxton can probably claim the best set of tonsils in soul-pop".Popmatters gave it a positive review, saying "The lead single sees Toni tapping into the recent success of female assertiveness (TLC, Kelis, Destiny's Child, and Pink) with the hit single “He Wasn’t Man Enough". Produced by the ubiquitous Darkchild, the track seems to be an attempt to make some headway within the lucrative urban R&B market.
"He Wasn't Man Enough" had peaked at number two on the Billboard Hot 100 the week of May 6, 2000 and stayed there for several weeks. The song also peaked at number one on the Hot R&B/Hip-Hop Songs for four weeks. The song had debuted at number five on the UK Singles Chart on its issue date of 29 April 2000. The song had debuted at number six on the Australian Singles Chart, until it eventually peaked at number five in that country. The song had debuted at number 36 on the New Zealand Singles Chart and later rose to number five after seven weeks on the charts. The song received platinum by the Recording Industry Association of New Zealand (RIANZ), selling over 15,000 copies there. The song had debuted at number 99 on the French Singles Chart until it fell out. Then it re-entered at number 74 on the charts and eventually peaked at number fifteen, becoming the biggest jump of the issue date of 1 July 2000. The song had debuted at number 21 on the Dutch Top 40, until it peaked at number five on their charts, staying in there for seventeen weeks.
The video, directed by Bille Woodruff from February 25–26, 2000, starts out with Braxton as an animated superhero who unzips her shirt to ward off villains. Next, she is shown dancing in a red cylinder-like hallway. The shot turns to a club where her ex (played by Braxton's former husband Keri Lewis) and his current wife (played by Robin Givens) walk in. Givens looks Braxton up and down and flashes her wedding ring at her. Braxton scoffs because she'd had him first and knows what a cheat he is.
The video flashes between Braxton dancing in the hallway and the club scene. At one point, the two women are in the club's bathroom, and Braxton lets the new wife know why she dumped her husband. They set up an act, wherein Braxton goes into a private room with him and gets him to drop his pants; all the while he is on camera, and everyone at the club, including his current wife, is watching. At the end, Givens busts in and throws the ring at him, and the two women give each other a high five.