The appearance of songs including featured artists on Billboard’s Hot 100 music charts has increased exponentially in the past two decades. This particular type of creative collaboration involves one artist integrating another artist’s contribution, either instrumentally or vocally, into their work and publicizing it with a “featuring” credit. According to broad literature in sociology on categorical boundaries, artists who deviate from existing genres are expected to be penalized for violating collective expectations and norms. We find songs featuring other artists actually have a greater likelihood of making it into the Top 10 than songs not featuring other artists. Additionally, consistent with theorizing about congruency in the cobranding literature, we observe that the greater the difference (cultural distance) between the genres of the artists involved, the more likely the song is to reach the top of the charts. We argue that by combining the expertise of specialists in each genre, as well as comingling audiences while still maintaining each collaborator’s original positioning, artists who feature artists from other genres are able to produce more successful songs.