The Hollywood Handbook Boys, Over 500 Episodes Deep

On May 16, Sean Clements and Hayes Davenport released the 500th episode of Hollywood Handbook, an insider’s guide to kicking butt and dropping names on the red-carpet-lined back hallways of this industry we call showbiz, with guest Ben Stiller. First launched on Earwolf in October 2013 as a quasi-spinoff of Clements and Davenport’s The Reality SHOW Show, the podcast has since become known as one of the great impossible-to-explainers in modern comedy, a shaggy, shape-shifting improv machine heavy with fan-maintained lore and nonsense inside jokes — for example, that Sean is in a troubled marriage to tennis legend Steffi Graf while Davenport is divorced from Brooke Shields.

At its core, Hollywood Handbook remains essentially a mockery of entertainment niceties — with Clements (mischievous, smirking) and Davenport (droll, unamused) taunting industry bigwigs from Donald Glover to Aubrey Plaza to Jon Hamm about whatever projects they are promoting, all while pleading to be involved with them. But it has quietly grown into an exploration of “friendship” in Hollywood and the ways the expected standards of professional collegiality — or, more specifically, the struggle to maintain them under constant bombardment from clowns both literal and figurative — are inherently ridiculous.

Given that, perhaps it’s no surprise that as long as the show has aired, so too has the argument that it is designed only to satisfy an acquired taste. But this is pure mythology. Those who have spent any part of the last decade with “Hayesman” and “the Clemdog” know that the show has only grown more arresting in recent years. Longtime listeners have come to count on recurring guests like Tom Scharpling, Ayo Edebiri, and Julie Klausner to play along so well that Clements and Davenport collapse into laughter before they can even establish an episode’s premise. The show draws from a core of squirmier regulars, such as Sona Movsesian or Esther Povitsky, who return despite their evident discomfort with the hosts’ comedy pincer attacks (only to find themselves asking again and again on air why they ever returned at all). Even the few episodes in which obstinate guests truly do not “get” the show have become fan favorites — especially for listeners who find the sound of Davenport spewing a disgusted “Bye!” funny.

After leaving Earwolf to found their Patreon, The Flagrant Ones, with Carl Tart in 2020, “the Boys” joined the Headgum network in May 2023 and celebrated with a sharp tongue-in-cheek takedown of co-founder Amir Blumenfeld. They instituted Try Month, a now-annual tradition in which they and their loyal producer and honorary “Third Boy,” Kevin Bartelt, make efforts to boost the show’s fan base by booking serious celebrities. The result is an ongoing renaissance of both creativity and popularity, of which the Stiller episode is only the most recent example. In the days following that milestone’s release, Clements, Davenport, and Bartelt hopped on Zoom to reflect on reaching their not-quite-second wind at Headgum, securing recent superstars like Adam McKay and Mackenzie Davis, and the future of audience-supported podcasts like theirs in the era of multiple Hollywood labor strikes. These are edited excerpts from our conversation.

You just hit your 500th episode, but you have threatened to quit a million times before. Do you think that has legitimately kept people away?
Sean Clements: We joke about not being satisfied with the listenership, or we’re like, “Don’t get invested. If you’re enjoying the podcast, you suck, because we think it’s bad.” That has had an adverse effect. So many people have started to say, “I wish they still liked doing the show.” They believe we want to quit and hate doing the show and feel some obligation to do it. But, of course, I love it! Why else would we do it?

Hayes Davenport: Telling people all the time that we’re going to end the show is part of the way we maintain the zero-growth mindset. When we said we were ending the show at 200 episodes, a very significant chunk of our audience believed that we had ended it — and were fine with it! They unsubscribed and only found out years later that we were still doing it.

S.C.: They were like, “We loved this show, but it’s time. They need to move on.” It’s like when somebody has a brief breakup with their significant other, you say how you really feel about them, then you get back together.

Yet you have recently launched some of your best episodes ever with huge celebrity guests, and Ben Stiller was a particularly fascinating one. Did you think about holding that episode for Try Month?
S.C.: I was helping out with this commercial Ben Stiller was doing that Rajat Suresh was in, and Ben was like, “I guess I’ve got to check out this podcast.” Then he mentioned that he had started listening to the show, which was terrifying. The very first reaction he had was, “Boy, you guys are really speaking your own language on that thing,” which was a fair response. I tried to underplay it, because I would have been embarrassed if he didn’t like it. But he mentioned listening to it again later and specific episodes that he enjoyed. Hayes said to me, “If he tells you that he’s listened to the podcast again, you are legally obligated to ask him if he’d like to do the show.”

And he did bring it up again, so I said, “It goes without saying, if you’d ever like to do the show, we’d love to have you.” He was like, “Totally, let’s do it,” which still felt to me like this might not happen but was just a nice thing to say? This happened prior to Try Month, and I did mention that to him, but he was very busy directing Severance. Then there was even more lead-up to the 500th, so I reached out again: “Hey, I know you’re busy, but is there any chance that sometime in the next six or seven weeks we could get an hour of your time so this could be the 500th episode?” And he was totally accommodating.

This milestone happened just as you are moving on to a new podcast network. I was surprised when you joined Headgum, because you had been with Earwolf previously, then decided to go independent on Patreon. What changed?
H.D.: With all these questions about our bookings or which networks we’re a part of or not, you are assigning a level of intention to it that I appreciate but is kind of not there. With Stiller, there was a lot of effort trying to get him on the show. For us and the level that goes into a normal episode, that’s a milestone episode. For Comedy Bang! Bang! that’s episode 46. We really enjoyed our time on Earwolf, but the different corporate shake-ups over there led to the point where our contract wasn’t really working for us and especially for them. Their business model is predicated on listener growth, which is not really our thing.

So it made sense for us to get on Patreon. We needed to reward our most engaged listeners and allow them to reward us. Then when it came to Headgum, they were really receptive to us continuing to have a Patreon. We just love incorporating a workplace into our episodes. All we really do is say what we see, so having more things, more people around us makes a better show. On Earwolf, we used to be able to talk about all of our grievances with our studio, boss, and engineer, and that’s something we lost on Zoom when it was just us and Kevin and our computers.

Kevin Bartelt: What’s been nice about being back in a studio as the producer is that I feel most confident when we have a few things banked and we’re not just doing things one day at a time, figuring it out as we’re doing it. We have to be a couple of weeks ahead, always looking forward. I like that aspect, because we’re at our best when we’re not figuring out “What are we doing tomorrow? Who’s the guest?” That adds a lot of stress to the show internally. Now that we’re back in studio, we’re ahead of that curve.

H.D.: What Kevin wants people to understand is that the No. 1 thing that contributes to the show’s quality and creative capacity is booking in advance.

You recorded a couple of episodes at Forever Dog too. Was that in consideration as a network to join?
S.C.: People were mad that we were on Zoom for a long time — unfairly, I think, because a lot of those episodes are good or at least what constitutes a good episode for us. But we did want to find a network that had a studio that we could use for our recordings, because it felt like that was important for our listeners, and it was starting to become viable for us to do again. I had a job in the valley. Hayes was working near there, too, and it was really close to the Forever Dog studios. Then someone at Headgum reached out and was like, “Hey, if you’re trying out other networks, please come check us out too.” I know this sounds like such a lazy thing, but since I was not working in the valley anymore and Headgum was a lot closer to Hayes’s and my houses, we thought it would be a lot easier to do Handbook there. And we don’t care about Kevin.

The Patreon world has been dangerous for podcasts lately. How have you found working with Patreon?
S.C.: I’ve had a generally positive experience. I don’t want to call it a second wind, but I do think we have had periods of reenergizing and finding new things to tackle and new bits that we’re excited about. That gets reflected in the Patreon, where we have seen people sign up in the last couple of months, as we’ve been doing bigger things and reinvesting in trying to get big guests like Stiller.

H.D.: In terms of being reenergized creatively, I don’t think we have that much control over it, because lack of effort is kind of the premise of our show, so we cannot betray that premise by working too hard on it or doing too much. I genuinely think our listeners respond to that negatively. It has to be something that’s happening in other parts of our lives that accidentally motivates us to do more on the show. Patreon is perfect for a show of our size, because we will never make money with a three-cent CPM on ad sales that they buy from us using an algorithm. We have a few thousand listeners, and a certain percentage of those are willing to pay for our work.

S.C.: Ad-supported revenue is completely based on the raw numbers of how many listeners you have, and we’re never going to have that giant appeal. Doughboys is one example, and when we were first at Earwolf, it was How Did This Get Made? It had people you knew from TV talking about movies you’ve seen. It’s so easy to access, and of course, they’re funny and their shows are fun. But we’ve never had … like, I still get a panic attack when somebody says, “What’s your show about?”

I am always baffled by this. Your show isn’t that hard to explain: It’s about guys pretending to be smart and being stupid and sarcastic about Hollywood with their guests in the middle of it. It’s not like I’m just “on your level” and others aren’t. This is not my “special show.” It is just constantly hilarious. Yet I feel like that gets lost a lot of the time, because there are so many gags about it constantly failing or not having a good listenership.
H.D.: Well, your outlet called us “deeply alienating,” and we put it on a T-shirt.

S.C.: One thing is that, as you said, you’ve listened from the beginning, so there’s no barrier in that way. And, yeah, maybe some of us calling the show bad and saying that it’s failing does incept the listener with that idea. It’s not my experience that it’s accessible. We have so much data of fans of the show going, “I have a lot of friends I think are smart and funny, and I just cannot get them into Hollywood Handbook.” There’s something that doesn’t click. Whatever. I accept that. Maybe it’s that there is no other access point for us, whereas with so many podcast hosts, you have some other concept of them before you start listening and like them before you even hit play.

The show has changed. It started out as us pretending to be Hollywood big shots who talked about our careers and these fake résumés we had. Then we moved away from that, and it became about being jealous of other podcasts and obsessed with the Doughboys being more successful. Then there was this whole period during Zoom when we were almost like PR consultants reading people their own press and media. That started with the Scott Aukerman one, where we watched his appearance on 60 Minutes and told him what he should have said.

Another thing that might turn people off is that yours is the only show I’m aware of that, when you bomb with a guest, can be funnier than when you’re trying your hardest. How does that impact people who are hoping for you to fail a little or for the guest not to “get” it?
S.C.: There was a whole period when there was curiosity around whether the guest was “in on it” or if they actually understood or “got” the show. Of course, our fan base primarily accused our female guests of not getting the show, which we asked them not to do anymore. But for the most part, an episode with a Pauly Shore — where the guest has zero concept at all of us or the show and is completely unwilling to play ball or figure it out in any way — is an outlier for us.

Can your fans discern between the Adam McKay episode, where the guest is really vibing with you and messing around in the negative, and, say, the Kurt Vile episode, where the person isn’t quite in the vibe you’re trying to create?
S.C.: Some people really enjoy the episodes that feel a little more awkward or almost like a prank on the guest. Kurt Vile I don’t think was prepared for what it was and I don’t think enjoyed what it was. Now, I really like him and his music — he’s a sweet guy. To know that afterward, he wished he hadn’t done it? That didn’t make me feel good. But 85 percent of the guests say at the end, “Is that what the show’s supposed to be like?” “Is it always like that?” “Was that okay?”

H.D.: Even people who have done this show multiple times.

I do feel that the show puts a lot of stock in embarrassment. You two being made out to be fools is of great delight to the audience.
S.C.: The characters that we are when we are hosting try to enter from a high-status place and, very often, get put into a low-status position and become pathetic worms over the course of the show, and I think that is funny, fun, and good. But we do want to be able to keep doing the show, and we do want guests to want to come on the show and enjoy doing it. Like, we didn’t know Adam McKay at all, and it felt like he had a fun, positive experience, which was really exciting for us. Maybe he’ll do the show again or tell other people, “These guys are really funny!” That is still our goal.

You’re both WGA members. How have the WGA strike and the impending SAG strike affected the show? 
S.C.: I actually told Kevin, “Hey, I just saw this person on the picket line two or three days ago. So I know that they are in L.A. and not working. Maybe they’d want to do something. Will you reach out to them?” We have been able to get ahead on scheduling, which Kevin thinks is the most important part of the show …

K.B.: By far.

S.C.: As we’re talking about guests and WGA, should I exclusively premiere this other podcast?

K.B.: Yeah!

S.C.: I’m starting to record a couple episodes of this other show. Because I’ve just been talking to many other writers about this strike and the state of the industry, we’re going to do a miniseries of me sitting down with other WGA members and watching movies about writers and Hollywood. Hayes and I talk about Adaptation for the first episode. I’m calling it Subtitles On, and the idea is that you’re “reading” the movie. It was written and, therefore, meant to be read. People are available for that. I don’t know if he’ll do an episode necessarily, but I ran into David Goodman, who’s on the negotiating committee, mentioned that I was doing this, and he was like, “I would love to do that.” It’s a good way to discuss the current state of the writing industry and do a movie podcast, which no one has ever done before.

H.D.: We are very well-suited for a strike environment, because we have never picked up a pencil to do the show.

S.C.: When we did the Podcaster’s Promise series, we had said we were going to write out an actual script and really do it fully produced. That became Hayes writing a one-paragraph intro that we recorded every episode for four episodes. People got mad about hearing it again and again. That was as much prep as we’ve done.

H.D.: My day job is not in comedy or entertainment anymore. But with the strike, I do feel that doing a show like this might be the future of creative work. As the studios don’t see the same profit potential in scripted entertainment, this sort of self-started, project-based employment might just be what doing comedy is like going forward. It took us many years to build and actually be able to make some money off it. I see more future in subscription-based entertainment for a smallish number of people than I do for a network comedy show that’s for millions. In that sense, we feel very lucky to have started doing this when we did.

Do you see another 500 episodes in your future?
S.C.: I don’t know how Hayes feels, but I’m starting to feel old, and I don’t want to be an old loser making a comedy thing that’s not funny. I joke about it on the show, but we’re in the middle of a streak, and at some point, we’ll record an episode and I’ll be like, “I did not have my fastball today.” In my career as a writer, and even doing whatever amount of performing I’ve done, I’ve dealt with a lot of disappointment and an inability to control the outcome of certain things. Pathetic as it is for a podcast with a very limited listenership, I don’t feel like I’ve ever had any other avenue to put my comedic voice out. Hollywood Handbook is the only thing that truly represents my work and my voice, along with Hayes’s, and I’m proud of it. So I can’t think of a reason for me to stop doing it. Unless we didn’t make money off it anymore, because it’s really just about money for me.

H.D.: The shabby preparation of it is what makes it sustainable for us. I feel like I could do it forever. Yeah, it will have its peaks and valleys, but it’s never been the thing where I need to stop doing it to make space for other stuff in my life. Continuing to do this allows me to do other things as well. It’s nice to keep listeners on their toes, that we could stop doing it at any time, but right now, I don’t see why we’d ever quit.