Can I Kick It?

The third single from the debut, released in October 1990 by Jive, was recorded in 1989 when the members were 18 and 19. It is built on a call-and-response chorus, and its samples include Lou Reed's Walk on the Wild Side, Ian Dury and the Blockheads' What a Waste, Dr. Lonnie Smith's Spinning Wheel, Prokofiev's Dance of the Knights and Sunshower by Dr. Buzzard's Original Savannah Band. Phife Dawg said that because of the Walk on the Wild Side sample the group received no money from the single, and that Lou Reed took the profits. In his second verse Phife Dawg asks Mr. Dinkins to be his mayor, a reference recorded before David Dinkins was elected.

The video was directed by Jim Swaffield and filmed in New York City, with De La Soul among those appearing. The group kick the word it across a film set, a park under the Williamsburg Bridge and a construction site. NME ranked the song number 90 on its 100 best songs of the 1990s in 2012, and Pitchfork placed it at 25 on its list of the 250 best songs of the 1990s in 2022. Rolling Stone ranked it number 292 on its 2021 list of the 500 greatest songs. It is the song logged most often: it appears in 43 of the 64 logged setlists that list songs, from the Apollo Theater in New York on 27 October 1990 to the group's final concert in Dorset on 9 September 2017. It has also been used in Tony Hawk's Pro Skater 1 + 2 and in the film Tom & Jerry.