This past year Dugan O’Neal has directed an impressive streak of videos that manage tone-perfect satire before veering off to unexpected places. For Haim’s “My Song 5,” he combined tabloid-talk-show sensationalism with Paul Thomas Anderson’s San Fernando Valley anxiety, then threw a witchy dream sequence in the middle. In Chromeo’s “Old 45’s” video, he elevated and undercut beer commercial clichés with Ryan Heffington choreography and a barroom brawl. And with “NRG” by Duck Sauce, he took infomercial nonsense to its inevitable, absurd endpoint. O’Neal also makes pretty, moody videos that are nice to look at, but he is best known for his comedic work that plays up the ridiculousness and tiptoes to the line of total insanity.

His videos also routinely feature cameos and appearances from other celebrities, guaranteeing easy headlines for website editors. “Song 5” not only starred Vanessa Bayer as host Dallas Murphy, but also included actress Artemis Pebdani, Kesha, Grimes, Vampire Weekend’s Ezra Koenig, Big Sean, and others. Haim then turned up in “Old 45’s” along with actor Jon Heder, while comedian Jon Daly took the lead role in “NRG.”

O’Neal grew up around the Monterey Peninsula on the Central Coast. His mother is an artist and his father is Tom Gundelfinger O’Neal, a rock-and-roll photographer who did some early videos for Steppenwolf and a bunch of album covers in the 1960s and ’70s. His parents have a photography business, so when O’Neal was growing up, he spent a lot of time assisting and learning from his dad. At the end of high school around the turn of the century, O’Neal realized he wanted to be a director, just as digital filmmaking software was becoming widely available. Before music videos, he was making comedic shorts, which he’d often perform in; now he pops up in the videos he directs, most notably as the photographer in Matt & Kim’s “Let’s Go.”

Though his videos regularly rack up impressive YouTube play counts and are awarded Vimeo Staff Picks, the music industry has changed so much from when O’Neal first got interested in the form that it’s tough to measure what a successful video director is. There isn’t really an MTV rotation to break into; everyone’s budgets have been slashed. O’Neal grew up loving guys like Spike Jonze and Jonathan Glazer, but the path these 1990s directors followed from music videos to commercials to feature films may not even exist anymore.

O’Neal talked to Grantland about his recent string of music videos and how he sees his career progressing.

How did Haim’s “My Song 5” video come together?

We shot the whole Dallas Murphy segment of the video as if it were an actual show. We shot it at these stages in Glendale where they do those kinds of shows, so they have those kinds of cameras there, tethered into a control room. We just set up the scenarios and let them act out the scenes.

Were the ones that are in the video all the ones you shot?

The only one where there wasn’t much going on was the one with Kesha and the cat. Everything else, they were kind of like mini scenes. I just took the most dramatic moments from each one.

Where did the concept for that video come from?

That concept is something I’ve been wanting to do. I wrote a treatment for the Black Keys three or four years ago, and I pitched them that idea. I went back and read the treatment and there were a few things that were subtly different, but it’s the same concept, where there’s the drama on the show that’s tonally quirky and funny, and then there’s the juxtaposition of the more cinematic, almost like Magnolia scenes, showing that there are these story lines both on the stage and backstage.

I’ve known Haim for a couple years and we’ve been talking about doing a video for a while now, and they hit me up. I got a call from the video commissioner at Sony, and he basically pitched the idea that they want to do something with a talk show like Jerry Springer or Sally Jessy Raphael. It was sweet, because I had been wanting to do a video like that for a long time.

That’s why I love when a band reaches out directly, and that’s how all the videos I’ve done this year have been. It’s just so much nicer to be like, “What are you thinking about? What’s inspiring you guys?” Most of the time you’re just throwing it out there into the wind, you have no idea. And most of the time there are 30 directors throwing ideas out there. It was like that for the Black Keys, and I never heard from them ever again.

How many days did that Haim video take?

That was a one-day shoot. They had to get extra funds because it was important to the band to have a live audience. If you don’t have enough money to get a whole crowd in there, it can look really cheap. They ended up finding more money, and we got 50 extras. That was the first time I’d ever done anything like that, and the energy of it was really fun. We had a whole crowd of people laughing when it was funny, and everyone just got into it. We were covering it with three cameras, so we could sit back and let these scenes play out and let the audience do what they would actually do on one of those shows.

And you could coordinate all those cameos in one day?

Yep. It took a lot of strategizing. There are so many different elements — the audience, the guests on the show, the host, the stuff backstage — so we talked about how it’d be awesome to get other people to be in it. All the musicians were friends with Haim. They got them. From the beginning, they said that Kesha was down to be in it. The main thing we were concerned about was the host. Vanessa came on board at the last minute.

But honestly, the only one I knew for certain on the day of the shoot was Kesha. When were shooting, it was crazy, because every 15 or 20 minutes someone from the label would be like, “Yo, Big Sean is here and we have to shoot him out in about 10 minutes.” Then an hour later, they’d be like, “Grimes is here. We have about 30 minutes with her.” So we’d have to find something for Grimes. A little bit after that, they’d say, “Ezra’s here, and we only have Ezra until noon.” We were working with a lot of different parts, but the shoot was actually really smooth and super fun.

How much direction did you give Vanessa in terms of her character?

We talked about it in the morning, and I gave her references. You don’t have to do much for someone like that. You need to just steer them in the right direction.

I know you’ve appeared in some of your videos. How did that start?

I started as a director, and then I became an actor because of that. I don’t like waiting or relying on other people, and a lot of times whenever I had an idea and there was no one around, I would just do it. Through that I found my own comedic voice. I do a lot of performance stuff now. It’s not something that I’m putting a lot of focus on because that’s a full-time job, trying to be an actor, and auditioning is the worst thing in the world. So it’s more just when friends ask me to be in stuff.

Did Chromeo come to you for the idea for “Old 45’s,” or were you among 30 people pitching ideas?

Chromeo obviously have an amazing sensibility, and they have great taste and have a very specific idea for what their visual aesthetic is. I met Dave, the lead singer of Chromeo, because I was in the video for “Jealous (I Ain’t With It)” — I play a cowboy. They were familiar with my work and liked a lot of my stuff. He’s A-Trak’s brother, and he was like, “He’s got a Duck Sauce album that they’re trying to do some videos for.” Within the next week, I met up with A-Trak.

When we were working on the idea [for “Old 45’s], he had a lot of really good ideas. They were going to do this project with [online boutique] SSENSE and, because it has to do with fashion, he wanted to do something with a highly cinematic editorial look. He had the idea of doing the desert and the Cindy Crawford ’90s Pepsi commercial. That was the reference. Then at the same time, we had to spin it so it wasn’t just a total ’90s parody. Then he had the idea to have them walk into the bar and it turns into a brawl. Then I filled in the rest and did what I do.

For the reference, I thought it was ’90s beer commercials.

It’s both of those things. The outside part is the Cindy Crawford, the inside was those Budweiser commercials with the spinning fan and yellowish windows with the sun coming in. I’m really influenced by that era, as well. I love those colors and the visuals, so a lot of my stuff looks kind of retro because of it.

How was that video to make?

It was one long day. It was fun, but it was a little bit challenging because it was 100 degrees where we shot that and we had all the lights, so inside it was really warm. When I’d walk outside, I’d be like, “It feels so nice,” but then I’d realize it was 100 degrees.

Were Haim and Dave from Chromeo regretting their leather jacket choices?

Dave didn’t complain at all. He was solid. I actually saw Chromeo play last night, and he wore a leather jacket the whole time. I think he’s used to it. I felt more for Haim. And P[-Thugg of Chromeo] had to wear that huge jacket the whole time.

Has the response to those videos been what you expected?

The Haim video was more than I expected. Because there were so many names in it, it made it easy for a lot of the blogs to talk about it. There was a lot of reach with that video. It was really cool to see Jerry Springer and Sally Jessy Raphael tweet about it. The response was equally as awesome with the Chromeo video as well, but it didn’t quite have the same impact. Because there are so many cameos in that Haim video, it took over the Internet for a day.

How much of do you feel the need to have special guests in videos to get attention?

I don’t think it’s necessary, but if it makes sense with the song, I’ll do them. I really love doing narrative things, and with Duck Sauce, Haim, and Chromeo, I liked treating them almost like the web series and short films that I’ve done. It’s bringing in another element to it, which can break up the song a little bit. When you’re doing that, working with people that I’m a fan of, it just makes it even better. When you have Vanessa Bayer or Jon Heder or Jon Daly on set, you give them just a couple notes or ideas and they’ll take it way farther. Obviously, the blogs will talk about it a lot, but it’s more of a selfish thing. I just really want to work with those people.

I can understand why you would want to do it, and I can understand why the artists would want to have them, but why do these actors want to do it? What do they get out of it?

Jon Heder is an überfan of Chromeo, so he was so pumped to do it. Jon Daly, I think he was just down. Haim is friends with Vanessa. But I don’t know. It’s not like they’re getting financially compensated. It’s more about doing a fun project with a band that they like.

Are you getting commercials off of your videos, or do those function as two separate worlds now?

The music videos definitely help with the commercials. It’s funny: In the commercial world, if you don’t have a commercial reel, then it’s tough to get commercials. But when you make things that are very specific to your voice, then it’s always going to help you get more things, whether it’s a commercial or something else. If it’s a good video for a cool band, it’s always going to help.

In the 1990s, it felt like there was this path where directors could go from music videos to commercials to movies. Does that path still exist?

For sure. Everything is changing and it’s not like there’s a path that everyone takes. The movie business has changed, the music business has changed, but because of the Internet, there’s no excuse to not get noticed if you’re making super-good things that are authentic and from the heart. All you have to do is make it, and you have all these tools to do it. That’s still definitely a path.

Is that the path you see for yourself?

I’m open to however my path plays out. I’m trying to not be too attached to how I see things going. For me, it’s just about continuing to make things that make me happy and also taking time to develop things that are bigger than a music video or a short film, that will have more legs or have more reach.

I like music videos and commercials, but soon I’d like to do more longer-form narrative stuff. I have some episodic TV ideas and some movie ideas. It’s just about choosing one and really seeing it through. I’d like to have a show where I could create content and act in it, too, someday. Commercials will always be there for directors, because it’s the most lucrative way to do what you love and make money, so you can invest time and energy into your personal projects.

Eric Ducker (@ericducker) is a writer and editor living in Los Angeles.

This article has been updated to correct the name of one of the people who appeared in the “My Song 5” video. It’s Artemis Pebdani, not Aidy Bryant.