Hip-hop and Hollywood aren’t strangers. Dating back to seminal rap-centric films such as Wild Style (1983) and Krush Groove (1985), the culture has long been using the cinematic medium in memorable ways. There’s also the long-running list of rappers turned actors, as well as album titles named after movies and several flick-derived MC names, all further blurring the line between the two art forms.

While A-listers in the film industry haven’t always acknowledged the hip-hop culture, one iconic filmmaker who’s never been shy about his rap Jones is Spike Lee. Just look at what he’s doing tomorrow: the Brooklyn-bred, big screen giant is set to direct a live webcast of The Roots & John Legend’s concert inside New York City’s Terminal 5. The show is in honor of the artists’ new collaborative LP, Wake Up! (which also happens to be a popular quote from Lee’s 1988 film School Daze).

What other legendary filmmaker would do such a dope thing? As much as we’d love to see Quentin Tarantino direct a Wu-Tang Clan performance film, we’re not holding our breath for that. Tomorrow’s webcast just proves how hip-hop Spike Lee is, in addition to adding another chapter to his history of contributions to the rap world. Here are 10 of his past moves.