While his output has slowed in these recent years, aside from the ambitious and thoroughly dense DROGAS Wave album, has earned his place in the annals of hip-hop history. Arguably one of the most brilliant writers in the game — at least on a conceptual level — Lupe’s early projects like Food & Liquor and The Cool went a long way in easing his layered messages to the casual listener.

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Along the way, the Chicago wordsmith made plenty of connections with his fellow emcees, as evidenced by this epic crossover throwback pic. Taking to Instagram, Lu showcased a photograph from April 24, 2006, taken backstage at the BET UpFront 2006 in New York City. The image finds him linked up with a pair of hip-hop icons from two generations, and .

“Westside Chi, Hollis & Jamaica,” captions Lupe, alongside the picture in question — curiously enough, both himself and 50 seem to be engaged in a heated thumb-wrestling match. And while these three rap titans never connected in the recording studio, it’s still cool to see them recognize one another as artists and equals — for some context, 2006 was the year 50 dropped Curtis, LL dropped Todd Smith, and Lupe dropped Food & Liquor. Check it out for yourself below.