“I Wish” I had another hit! Skee-Lo’s debut single and signature song became an international hit, reaching the top 30 in several countries around the world including a #13 peak in the US in September 1995. It remains his only song to appear on the Hot 100, thereby earning him the label of one-hit wonder. One could say Skee-Lo is the Dexter Green of rap: an arguably minor, albeit unforgettable romantic figure.

Skee-Lo wrote the bulk of this song’s lyrics, sans music, during a study session in college. He added music after hearing the horn section “in the middle of an old, ugly record”. Soon after, he came up with the chorus lines after doing a freestyle in a parking lot.

In contrast to the bravado of most popular rap songs at the time, where rappers brag about their strength, their success with ladies, their slick cars, and overall flyness, this song’s lyrics are completely self-deprecating. Throughout the song, Skee-Lo openly laments a variety of personal and financial shortcomings that he blames for his failed attempts at getting a girlfriend.

Skee-Lo claims he never made a cent from the first five years of success of this song. In protest to his record label, he put his entire career on hold:

…they took all the profits. So I refused to shoot any more videos, promote or record music. I’m not their slave. I wasn’t working for free.