Entertainment TV A Look Back at Pete Davidson's Funniest 'Saturday Night Live' Sketches (So Far) Ariana Grande's boyfriend has been a cast member on Saturday Night Live since September 2014 By Karen Mizoguchi Published on June 4, 2018 10:20 PM Share Tweet Pin Email 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: Pete Davidson Gets 2 Ariana Grande Tattoos After Making Relationship Instagram Official NBC 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. Want to keep up on the latest from PEOPLE? Sign up for our daily newsletter to get our best stories of the day delivered straight to your inbox. 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 both Benedict Cumberbatch, Saoirse Ronan and Julia Louis-Dreyfus. And most recently, Davidson reprised his character for a sketch opposite Jessica 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 the The Devil Wears Prada star such a great actor. Tweaking the lyrics of Lil Pump’s “Gucci Gang” to “Tucci Gang,” Davidson channels the rapper’s sense of style as he raps about Tucci’s impressive film credits such as Beauty and the Beast, Spotlight, Transformers: The Last Knight and of course, The Hunger Games. Watch the full season of Search History on PeopleTV.com or download the PeopleTV app on your favorite device. High School Roles As the youngest cast member of SNL, Davidson has been in many sketches that have to do with high school-related material. From playing a goth kid for a graduation commercial to a student in a classroom talking about the national school walkouts and a career day sketch, Davidson has been cast in skits about youth. One of his youngest (and most hilarious) roles was seventh-grade social media influencer Dylan Maxwell at 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-throwing Jared Kushner in a This 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 been making headlines for his relationship with pop star Grande, which has been going strong since PEOPLE confirmed in May that the duo had started casually seeing each other since her breakup with ex Mac Miller. He recently just got two tattoos in her honor.