(Debuted March 4, 1989, Peaked #3, 18 Weeks on the Chart)
"Funky Cold Medina" is definitely a relic of the late 1980s. Built on top of a sample (from Van Halen's "Janie's Cryin'"), the song's lyrics mention Spuds McKenzie, the Love Connection TV show and even mentions the decade in one of its lines. A somewhat humorous look at dating, the narrator is relying on a potion to get lucky with the ladies but things keep going wrong. First, his dog gets the action. Next, he picks up "Sheena" at a club only to find out it was another man. Then, he finds a lady who wants to get married, which makes him get up and leave.
While it was a #3 hit, it was very similar in style, tone and subject to Tone-Loc's earlier hit "Wild Thing" and used the same guitar riff as its sample. While the kids definitely knew the difference, others may have thought they were listening to the same song. Even though both singles went platinum and the Loc-ed After Dark LP went to #1 on the album chart, the similarity may have killed his career momentum. He never had another Top 40 hit again.