Before his high-profile romance with Ariana Grande, Pete Davidson had made a name for himself on Saturday Night Live.

Davidson, 24, joined the cast of the NBC sketch comedy series as a featured player during the show’s 40th season premiere in September 2014. At 20, he was the first cast member to be born in the 1990s and one of the youngest cast members ever.

The Staten Island native had been doing stand-up comedy since his teenage years. Prior to his SNL debut, he appeared on MTV’s Wild ‘N Out in 2013 and nabbed a small role in Adam DeVine’s House Party that same year. He also made stand-up appearances on Jimmy Kimmel Live!, guest-starred in Brooklyn Nine-Nine and roasted Justin Bieber at Comedy Central’s 2015 roast.

Here are some of Davidson’s funniest highlights from his 219 sketches during his four seasons on SNL:

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Weekend Update

Davidson has become a frequent guest, joining Colin Jost and Michael Che at the Update desk with commentary from a “Resident Young Person.”

From talking about hair loss to millennial points of views on business and living with his mother, he has candidly shared his perspective much like his stand-up routines.

While many tap into sketch comedy characters for an Update cameo, Davidson is among the very few castmates, like Leslie Jones, who share their authentic views on topics discussed during the segment.

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