On Friday, August 7, late-night television will lose one of its most beloved hosts, as Jon Stewart retires from his 16-year tenure at the helm of Comedy Central’s flagship news-satire program, “The Daily Show.” Along the way, Stewart has lambasted politicians, society, corporations, and the average citizen in equal parts poignant critique and hilarious entertainment and his guests have run the gamut from Heads of State (President Obama visited him last week) to rappers like Snoop Dogg, Ludacris, Ja Rule, and others. The Hip-Hop influence extends beyond the MC-as-guest component, however, and the show embraced all of its elements in one form or another throughout the years. In celebration of Stewart’s legacy, here are some of the show’s most memorable Hip-Hop moments.

In the summer of 2014, all nine surviving members of the Wu-Tang Clan visited Stewart, filming a segment for the day’s episode in which they promoted their album A Better Tomorrow. The humor begins nearly immediately, as all nine members introduce themselves only to be followed by a tenth, comedian and “Daily Show” contributor Jordan Klepper who introduces himself as Jordan KlepperZA. The laughter doesn’t stop there.

Hip-Hop was incorporated into Stewart’s monologue in May in a way that was unexpected but nevertheless dope. In discussing the ever-growing number of Republican candidates running for president in 2016, Stewart comically attacks candidate Dr. Ben Carson’s choice of Eminem’s “Lose Yourself” as the soundtrack to his official candidacy announcement (sung by a choir). Stewart raps a couple of the song’s bars and continues into a piece of “Forgot About Dre.” Check out his flows.

Back in 2010, Jay Z stopped by the studio for an in-depth conversation about not only his then-recently released book Decoded, but also the Hip-Hop culture at large. In the extended interview below, the two touch upon Jigga’s goals with the book, Hip-Hop’s relationship with the police, the commercialization of the music, and more.

In a particularly powerful blending of the news and Hip-Hop, Stewart addressed the controversy surrounding the Oklahoma University chapter of the SAE fraternity and its racist chants. More specifically, he criticized MSNBC’s program “Morning Joe” and its panel for attributing some of the blame for the chants on the consumption of rap music. Stewart tears into his criticism, chastising the parties involved for suggesting a causal relationship between rap music and the behavior of those fraternity members. On March 11, 2015 (the same day Common stopped by for an interview), Jon Stewart fought for Hip-Hop in a very powerful way.

Other notable guests include RZA, Busta Rhymes, the Beastie Boys’ Ad-Rock, Wyclef Jean, and Queen Latifah.

Related: President Obama’s Final Daily Show Interview Brings Powerful Ideas On College Reform (Video)