"It's Tricky" is the final single released from Run–D.M.C.'s third album, Raising Hell. It was released early in 1987 through Profile Records and was co-produced by Rick Rubin and the group themselves. The song peaked at No. 57 on the Billboard Hot 100 and No. 21 on the Hot R&B/Hip-Hop Songs. In the UK, the song made #16 on the UK Singles Chart upon its original release and #74 in 1998, while the Jason Nevins remix of their song "It's Like That" spent its fifth week at #1. Two decades after the song's release, The Knack sued Run-D.M.C. on the grounds "It's Tricky" sampled their song "My Sharona" without permission.

The music video features Penn and Teller, who are hustling a group of people with a game of three-card Monte in front of the Rialto Theater in downtown Los Angeles. Run–D.M.C. are called and shut their business down by winning every hand they play. Penn then asks the group if they can teach them to dance, which they do after insisting that Penn and Teller change their clothes. The video ends with Run–D.M.C. showing up to a gig in Japan six months later, where they find the duo impersonating them; unable to tell the difference, the concert promoters deny Run–D.M.C. the chance to perform.

This song contains samples of "My Sharona" by The Knack, as well as the entire vocal structure from "Mickey" by Toni Basil. The Knack sued Run DMC over the track in 2006, and the lawsuit was settled out of court.

The Bloodhound Gang covered the song on their second album One Fierce Beer Coaster.

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