Before hishigh-profile romancewithAriana Grande,Pete Davidsonhad made a name for himself onSaturday 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.

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

NBC

pete-davidson

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 abouthair lossto millennial points of views onbusinessand 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.

Chad

Recurring characters have become a rarity in the past couple seasons, but Davidson has brought back his monotone bro character for several episodes.

Known as the somehow irresistibly attractive male character with a deadpan delivery, Chad has already wooed bothBenedict Cumberbatch,Saoirse RonanandJulia Louis-Dreyfus.

And most recently, Davidson reprised his character for a sketch oppositeJessica Chastain, who played a doctor falling in love with Chad.

Many fans continue to ponder: What is it about Chad?

Lil Pump

In January, Davidson and host Sam Rockwell dedicated an entire comedy sketch to Stanley Tucci in a music video parody that celebrated what makes theThe Devil Wears Pradastar such a great actor.

High School Roles

As the youngest cast member ofSNL, Davidson has been in many sketches that have to do with high school-related material. From playing a goth kid for agraduation commercialto a student in a classroom talking about thenational school walkoutsand acareer daysketch, Davidson has been cast in skits about youth.

One of his youngest (and most hilarious) roles was seventh-grade social media influencerDylan Maxwellat the 2018 Nickelodeon Kids’ Choice Awards.

Politics

Though Davidson has been part of many original characters, he has also transformed into several politicians and commentators.

Davidson played Jason Chaffetz in October 2015 and portrayed a Manischewitz bottle-throwingJared Kushnerin aThis Is U.S.parody in March.

The only political character he depicted more than once was Marco Rubio in December 2015 and January 2016 during the GOP debates.

Davidson has beenmaking headlinesfor his relationship with pop star Grande, which has beengoing strongsince PEOPLE confirmed in May that the duo hadstarted casually seeing each othersince her breakup with ex Mac Miller. He recently just gottwo tattoosin her honor.

source: people.com