It's Tricky

It's Tricky: Run-D.M.C. and the Art of Hip-Hop Self-Examination

The Group That Changed Everything

By February 1987, Run-D.M.C. had already rewritten the rules of what hip-hop could accomplish commercially and culturally. The Hollis, Queens trio had broken hip-hop into the rock mainstream with Raising Hell in 1986, produced the landmark Aerosmith collaboration that had made "Walk This Way" a genre-crossing radio staple, and demonstrated that rap music could fill arenas and sell millions of records. When "It's Tricky" entered the Billboard Hot 100 in late February 1987, it arrived as the work of artists operating at the absolute top of their creative and commercial powers.

A Song About the Performance of Hip-Hop Itself

"It's Tricky" takes as its subject the art of rapping and the challenges of maintaining freshness in a form that is hungry for novelty. The song's lyrical content is self-referential in a way that was still relatively unusual for chart-aimed hip-hop in 1987; it is a meditation on the craft of the MC, on the difficulty of delivering under pressure, on the experience of performing for an audience that expects something new every time. The track builds its energy through this meta-awareness, with Run and DMC demonstrating the skill they are also describing.

Ten Weeks and a Peak of Fifty-Seven

The single debuted at number 93 on February 28, 1987 and climbed steadily through March, reaching its peak position of number 57 on April 11, 1987 and spending 10 weeks on the Hot 100. As with many rap singles of the era, the Hot 100 peak did not fully capture the song's cultural impact; hip-hop's primary metrics were playing out in ways that the mainstream chart still measured imperfectly. The track's influence on the emerging generation of MCs was considerably larger than a number 57 peak might suggest.

The Production and Its Sonic Signature

The production on "It's Tricky" carries the unmistakable signature of mid-1980s Run-D.M.C.: hard, spare, and built for maximum impact at high volume. DJ Jam Master Jay's contribution to the track's rhythmic foundation gives the song its physicality, and the call-and-response structure between Run and DMC creates a conversational energy that pulls the listener into the performance rather than leaving them as observers. The use of a melodic hook sampled from a previous hit gives the track a familiar entry point without sacrificing any of its forward momentum.

A Song That Transcended Its Chart Position

The decades since 1987 have confirmed what a number 57 peak could not tell you: "It's Tricky" became one of the essential Run-D.M.C. tracks, appearing in film soundtracks, advertising campaigns, and as the model for subsequent generations of rappers who were drawn to its self-aware energy. The song's capacity to make the difficult look effortless, to treat the serious business of MC craft as something celebratory rather than burdensome, gave it a longevity that most of its chart neighbors from that week have not achieved. Run-D.M.C. at their peak were untouchable, and this track is the evidence. Press play and feel why.

The timing of the single within the Run-D.M.C. catalog was also significant. Raising Hell had been a cultural earthquake, and the expectations surrounding the group's next moves were correspondingly enormous. The decision to include a track that was partly self-referential and partly celebratory within a body of work that had also dealt with social and cultural weight showed the range of what the group was capable of. Hip-hop in 1987 was still establishing the vocabulary of what the form could say and how it could say it, and "It's Tricky" demonstrated that self-awareness and playfulness were as legitimate a part of that vocabulary as political commentary or social observation.

"It's Tricky" — Run-D.M.C.'s singular moment on the 1980s charts.