Summary

Collider’s Joe Schmidt talks with Anna Konkle and Derek Waters for Side Quest.

An unexpected return for Phil the art guy in Apple TV+’s Side Quest brings a blend of deadpan humor and poignant drama to the Mythic Quest spin-off series.

Waters and Konkle discuss balancing emotional weight with awkward comedy in the episode, showing Phil’s inner life.

The premiere episode of Apple TV+’s Side Quest kicks off the anthology series with an unexpectedly tender return to Mythic Quest’s most tormented background character — Phil the art guy. Played by Drunk History’s Derek Waters, Phil is back in the spotlight, this time navigating a spiraling work-life balance, anxiety, and the quiet hope of love in an episode that blends deadpan humor with poignant drama. Anna Konkle joins the episode’s cast as Julia, Phil’s grounded and magnetic yoga instructor-turned-love interest, whose presence challenges him to step outside his self-sabotaging habits.
In an interview with Collider’s Joe Schmidt, Waters and Konkle discussed how they balanced the series’ emotional weight with the signature awkward comedy of the Mythic Quest universe. Waters, thrilled to revisit a character he thought was gone for good, described the experience as a chance to show Phil’s inner life beyond the background jokes. Konkle, meanwhile, reflected on the surprising challenge of playing a more “normal” character and how the duo’s immediate off-screen chemistry brought heart and authenticity to the episode.
A New Chapter for Phil the Art Guy

“It was just fun to go back into the world of Phil…”

COLLIDER: Let’s start off with the reason why we’re here – Side Quest – which I am a big fan of Mythic Quest. And so, of course, the standalone episodes were a really, really cool thing to watch every single season. So to get a cool little anthology series with Phil the art guy and his eternally tortured presence on the show, and then also getting Anna, your character on there, and you are always such a bright spot in it. What appealed to you about this episode? And let’s start with Derek, since you’re returning to this character who just can’t seem to get away from an overbearing boss.
DEREK WATERS: I was so excited because I thought my character was dead. So I was like, “He’s alive? Great! I know I was let go. Oh, wow. And I can do an episode when I get to dance to a ‘Creep’ cover, that’s so good. And I get to work with Anna Konkle.” Anna and I had met, but we had never worked together, so I was so excited to get back working with Rob [McElhenney] and all the Mythic Quest people. But this was also so exciting to do drama, dancing, and work with Anna. Truly, like instantly hit it off. We started working on a project together after this and just became instant friends. I humbly think you can see how much we get along in the episode. It was just fun to go back into the world of Phil and be able to show his external feelings that have been so internal on Mythic Quest, to be able to show the outer part of a tormented man.
ANNA KONKLE: And it’s really fun, also, watching your dramatic acting, if I can just say. And seeing you on Mythic Quest too, it felt like such a no-brainer to see you lean more into drama. You’re so good at it. And also with the comedy, obviously. But I’m excited to see you do more of that.
WATERS: Thanks, Anna.
Anna, coming into this series, were you a fan of Mythic Quest beforehand?
KONKLE: I’m behind on literally everything, so I watched It’s Always Sunny in Philadelphia, which is incredible. So I jumped in and watched it before this, and it’s so good.
Balancing Comedy and Heartfelt Emotion

“It was different for me, playing more of a well-adjusted person…”

Image via Apple TV+

You play a really cool character, and you mentioned playing off him and acting in a more dramatic role, but your chemistry is pretty great. It’s undeniable that you guys are a very cute couple that you’re rooting for. For playing a role like this, it’s really cool to see your dynamic when he’s playing a workaholic ridden with anxiety and self-sabotage. So, how do you balance those types of things with the cute stuff that you guys are throwing in there as well?
KONKLE: Well, it’s fun. I usually play characters that my mom gives me feedback on, and she is like, “She was really weird. Why was she so weird? She made me uncomfortable.” That’s what my mom says a lot of the time. Hopefully, this one doesn’t make her uncomfortable. It was different for me, playing more of a well-adjusted person, but it was fun. And it was fun, the challenge of being the cutesy, charismatic woman in something gives me pause because I don’t think it’s easy, actually. To me, it’s a lot harder than being the weirdo in the corner that’s supposed to be funny. To be mainstream and normal and funny seems a lot harder to me.
So it was sort of intimidating, and it was great to know that we had the kind of connection that we immediately had, but I was intimidated going into it for that reason. And then it was just kind of downhill after the first yoga scene, because it was just fun and easy, and it was a good contradiction to each other, I think.
And Derek, you already mentioned the dancing – the very wonderful dance sequence and how that looked.
WATERS: But did I mention my goal was to be Björk inside of Chris Farley’s body? That was my goal.

Image via Apple TV+

What is up with Rob McElhenney shows in these intricate dance sequences that just completely blow out anything? Anyway, that’s a different question. I want to ask the same thing. Like I mentioned, you play a workaholic, you’re anxious because of the demands of the job, and the self-sabotaging aspect. How difficult is it to balance with the comedy of the tone? You’re obviously a dry character, but the show at its core is very funny and ridiculous in what it is presenting, so what was the challenge there?
WATERS: I humbly say, it was more of, “Oh, man, I get to do this,” more than a challenge. Because I think the best comedy has drama in it, and to be able to be like, “Oh, I don’t have to just sound stupid.” Not saying that Phil did, but most parts that I play are dummies and it was nice to show, “Oh, this guy’s tormented and has heart and can be fun.” There are a lot of funny moments, but I also think Anna is just such a good actor that I just played off of her.
KONKLE: So nice, thank you.
WATERS: I find it funny when two really funny people are being serious. I humbly didn’t think it was a challenge. It was just so much fun. Drama’s definitely not my normal acting, so that was just fun, though. I’ve always wanted the opportunity to be more serious about something, which is also how I got into comedy, because when I did stuff in high school, people would just laugh, and it wasn’t funny.
KONKLE: Yeah, I relate to that too. In the editing of PEN15, I remember being like, “Oh, the funniest moments are when I’m just incredibly serious.”

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Talk about a cliffhanger!

I have to ask both of you one more question. Because you’ve just mentioned PEN15, Anna, do you have another project in the works with Maya (Ishii-Peters) coming up that we can expect to see on screen? And then Derek, I also have to ask you, is there a chance Drunk History can return?
KONKLE: The short answer is with Maya, I think at some point there will be more, but our project right now is being best friends.
WATERS: Aw, I love that.
KONKLE: It’s a neat phase, actually, in life. Our kids are really close, and that’s pretty exciting. I have a TV project that I’m working on, and a book I’m finishing. I’m just trying to stay passionate and busy.
WATERS: And I hope Drunk History comes back. It has legal issues, just trying to get it back from Comedy Central, but I don’t see myself not doing specials every once in a while, once I am allowed to do that.
Side Quest Season 1 is now streaming on Apple TV+.