After nine seasons on Saturday Night Live, the time has come to close the chapter on Kyle Mooney.

Mooney joined the cast of Saturday Night Live for Season 39 in 2013. He was a featured player for two years before being bumped up to a regular cast member for Season 41.

Kyle has worked with Upright Citizens Brigade and has had a successful YouTube channel since 2005. He has worked with former co-star, Beck Bennett for years before they both landed the gig on SNL. He has also had roles in films such as Hello, My Name is Doris, Zoolander 2, and Brigsby Bear, which he co-wrote. He also co-created Saturday Morning All-Star Hits!, a Netflix original that spoofs 1980s Saturday morning cartoons, which had Kyle appearing as multiple characters across eight episodes.

Kyle is a master of the awkward, and he sure pushes it to the point of cringe. On SNL, his voice is very original, and he excels in the digital short format. Mooney’s quirkiness will sure be missed as it filled a void that not too many performers can fill. Alas, he will go on and produce his own unique brand of comedy in other places. In the meantime, here are 11 times on SNL when he was just so very Kyle that you can’t help but smile.

Weekend Update Bad Comedian Bruce Chandling (Recurring)

Weekend Update Bad Comedian Bruce Chandling

One of Kyle’s best-known recurring characters is a comedian who is really quite bad at stand-up. This character hits home because face it, we’ve all seen this guy. Bruce Chandling appeared six times throughout Kyle’s run, each time more agonizing than the last. In his signature leather jacket and mullet, Bruce is great at being bad and oftentimes takes a dark turn with a quick glimpse into his horrible life. As a frequent guest on Weekend Update, Michael Che claims Bruce was the one who got him started in the biz and is (fake) outraged at just how bad Bruce is.

Weekend Update: Bruce Chandling - SNL

Baby Yoda (Recurring)

michael-che-baby-yoda-weekend-update-featured

In 2019, Baby Yoda made his debut on The Mandalorian and Kyle played him on Weekend Update with a bit of a different take. Over the next six appearances, Baby Yoda (or Grogu) made it quite clear he was nothing like his onscreen persona. From his playboy lifestyle to his beef with Baby Groot, this was an appearance no one was expecting, but once it was here, we couldn’t get enough of it.

Weekend Update: Baby Yoda on His Spiritual Awakening - SNL

RELATED: 'Saturday Morning All Star Hits!' Trailer Shows Kyle Mooney Parodying Kids' TV

Behind the Scenes Kyle (Recurring)

Kyle is at his best when he does his fake behind-the-scenes shorts. He did a series where he was really putting himself out there to become a better person. Obviously in jest, Kyle strives to be less awkward (which is impossible) and do whatever it takes to make a good impression. In the first outing, “A New Kyle” (Season 44, Episode 1), Kyle thinks that this new season is going to be his time. However, over the summer, his co-star, Pete Davidson, happened to get engaged to Ariana Grande. So it’s pretty obvious who is going to get all the attention now. It’s time for a battle. In the second instance, “Kyle and Friends,” Kyle awkwardly puts in extra effort to make genuine friendships with the cast and hosts. It ends badly, especially for host Regina King who ends up getting stabbed. However, it is his last and most recent one that is one of our favorites. In “Kyle’s Transformation” (Season 47, Episode 13), Kyle is crestfallen when host John Mulaney pops in and asks Beck Bennett to appear shirtless in a stripper sketch he’s writing. Kyle takes it upon himself to hire a trainer (Justin Theroux) and really transform his body. The results are disturbing, and yet just so very Kyle.

Kyle's Transformation - SNL

Awkward Flirts (Season 39, Episode 17)

Awkward Flirts Vanessa Bayer and Kyle Mooney

In Kyle’s first season, he met his match with the reigning queen of awkward, Vanessa Bayer. In this sketch, Vanessa and Kyle are neighbors but both have a lot of trouble flirting with each other. Ever cringe worthy, the two go toe to toe, and it is difficult to say who is harder to watch. Once again Beck Bennett shows up to throw a wrench in his plans, but this sketch is proof that Kyle and Vanessa should have had way more time together as onscreen partners.

Awkward Flirts - SNL

Brothers (Season 44, Episode 5)

Brothers Kyle Mooney

Beck and Kyle are back together again as they play young brothers Jared and Spencer. Mom (Cecily Strong) and Dad (Host Liev Schreiber) are quite used to their fighting. But their new friends played by Kenan Thompson and Aidy Bryant are absolutely horrified at their raucous behavior. It’s only when Dad brings the hose out (yes, he keeps one in the house) that the boys even begin to come close to behaving. Besides, it’s always fun to watch Cecily and Aidy completely break.

Brothers Sketch - SNL

Leslie & Kyle (Season 42, Episode 8)/Love and Leslie (Season 44, Episode 21)

Leslie Jones & Kyle Mooney

The fictional love affair of Kyle and Leslie Jones was the gift that no one knew they needed. As Leslie waxed poetic about how tough it was to meet men and have real relationships, she surprises everyone with the news that she and Kyle have started dating. Kyle, the Cast, and even Lorne Michaels really want Kyle to lose his virginity, but he is mad with jealousy over Leslie’s flirtation with Colin Jost. The duo revisited their romance a few seasons later with an update. Not only had they gotten married, but they had a kid. Spoiler alert… they were having some troubles.

Love and Leslie - SNL

Scooter Rineholdt (Season 45, Episode 6)

Scooter Rineholdt

Another insane appearance on Weekend Update introduced us to Scooter, who is the president of Milk Distribution at Dean Foods. Scooter is OUTRAGED at the bad press that milk is getting with all these people choosing non-dairy milk. It sounds silly, but Kyle’s commitment is so fierce to chugging and spraying milk that Che can barely hold it together.

Weekend Update: Scooter Rineholdt - SNL

PottyPM (Season 45, Episode 8)

Potty PM

A commercial for a device that lets men go to the bathroom in the middle of the night without having to get out of bed. Sounds perfect, right? Kyle happily explains how men just have to attach the unit that connects to the toilet, so they can urinate comfortably throughout the night. Jennifer Lopez soon shows up and asks one simple question. How does it work for women?

PottyPM - SNL

Del Taco Commercial (Season 45, Episode 11)

Del Taco Commercial

Kyle plays Douglas, an actor who, along with Miranda (Chloe Fineman), has been cast in a new Del Taco commercial. They are super excited to work with the director (Bennett) and the VP of Branding for Del Taco (Host Adam Driver), who has arrived to supervise the shoot. When they do the first run-through, Chloe is perfection. Kyle, however, needs some work. And Bennett and Driver will stop at nothing to get him to give his best performance ever.

Del Taco Shoot - SNL

What’s My Name? (Season 45, Episode 17)

What's My Name

The lockdown of 2020 was tough on everyone. SNL did three “at home shows” with cast members doing virtual sketches, zooms, and shorts from the comfort of their own homes while the world was locked down. It was an experiment and some thrived, but none were stranger than Kyle’s video, which included a house party filled with people… all played by Kyle. It includes a musical number and weirdness galore, and it’s just something that needs to be seen to be believed, all while being a perfect encapsulation of Spring 2020.

What's My Name? - SNL

Bits (Season 46, Episode 7)

Bits

Is there anything worse than hanging out with a bunch of your friends, and they are so quick and so committed to bits, and you just can’t keep up? Kyle really hammers this sentiment home when he drives a bit into the ground to the point where his pals Beck, Pete, Mikey Day, and Chris Redd have to tell him to lay off. What’s the only next move? Internal musical number, obviously.

Bits - SNL