"It's Tricky" is the fourth single released from Run-DMC'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 US Billboard Hot 100 and No. 21 on the Hot R&B/Hip-Hop Songs. In the UK, the song reached No. 16 on the UK Singles Chart.

In 1998, American producer Jason Nevins remixed the song under the amended title "(It's) Tricky". This version peaked at No. 74 in the UK while Nevins' remix of Run-DMC's song "It's Like That" spent its fifth week at No. 1 on the UK Singles Chart.^[1] Nevins' remix also achieved top-40 placings in continental Europe, Australia, and New Zealand.^[2]

Two decades after the song's release, the Knack sued Run-DMC on the grounds that "It's Tricky" sampled their song "My Sharona" without permission.

Run-D.M.C's previous studio album King of Rock had established the group's fusion of hip-hop and hard rock (as well as their cover of Walk This Way by Aerosmith), which blossomed on Raising Hell. This was due in part to the presence of Rick Rubin as their record producer. Rubin had an affinity for metal and rap in equal measures and he knew how to play to the strengths of both. At the same time, he slipped in commercial concessions that came off as sly even when they borrowed from familiar songs, such as "My Sharona" on the single "It's Tricky."^[3] The 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.^[4][5] One notable element of the song was its anti-drug lyrics such as “We are not thugs, we don’t use drugs.”^[6]

Rolling Stone writer Mark Kemp remarked, "'It's Tricky' cribs the guitar part from the Knack's 'My Sharona,' a fatuous New Wave song, and turns it into vital street art."^[7] Pitchfork's Tom Breihan claimed, "Run and DMC had also stepped their rap game up; "It's Tricky" is basically as good as the two of them ever got, spitting quick-tongue witticisms and yelling booming threats with equal abandon."^[8] Time writer stated the song serves "to prove their ferocity."^[9] Commenting on the crossover appeal, AllMusic's stated, "Rubin loved metal and rap in equal measures and he knew how to play to the strengths of both, while slipping in commercial concessions that seemed sly even when they borrowed from songs as familiar as 'My Sharona.'"^[3]

The music video features Penn and Teller hustling a group of people with a game of three-card Monte^[10] in front of the Rialto Theater in downtown Los Angeles. Run-DMC 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. Six months later, Run-DMC show up for their gig in Japan, but are denied entry as Penn and Teller are already on stage impersonating them.

The song is used in the promotional clip for the FX television series Snowfall, which began airing in July 2017.^[11] The original song appeared in the movies Road Trip, Can't Hardly Wait, Turbo, White Chicks, The Bounty Hunter, The Boss Baby: Family Business, Sonic the Hedgehog 2, in the television shows One Tree Hill and King of the Hill, and in the video games WWE 2K16, Forza Horizon 3, and SSX series, SSX Tricky in particular, being named after the song.^[12][13] In 2021, the song was sampled by Crazy Frog.^[14]

7-inch

• A. "It's Tricky" – 3:02
• B. "Proud to Be Black" – 3:14

12-inch

• A1. "It's Tricky" (Club Mix) – 7:19
• A2. "Up Tempo" – 2:35
• B1. "It's Tricky" (Remix) – 4:31
• B2. "It's Tricky" (Scratchapella) – 3:51
• B3. "Tricky Reprise" – 2:54
• B4. "Proud to Be Black" – 3:14