For nearly thirty years, Robert Smigel’s Triumph the Insult Comic Dog has been ripping into people of all different walks of life. A veteran of Saturday Night Live, Smigel’s foul-mouthed puppet persona has become one of the most enduring comedic characters of the 21st century. No one’s safe from Triumph — but it’s far from Smigel’s only creative outlet, as he’s also been a major creative behind the scenes for animated films like Leo.

2024 has been off to a strong start for Smigel, with the latest installment of his “Let’s Make A Poop” mock-game show coming to Youtube with Adam Savage, Rob Schneider, and Weird Al Yankovic as the targets of Triumph’s jabs and jokes. It’s not the only video courtesy of Smigel lately either, with Tiffany Topal and dancing lizards giving a goofy music video for Leo the Oscar treatment. During an interview with That Hashtag Show, Smigel discussed the origins of the “Last Minute Oscar Highlights” video, the most enjoyable part of bringing back Let’s Make A Poop, and his favorite subjects to mock with Triumph.

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THS: Starting off, I’ve got to ask — which celeb cutaway was your favorite in “Last Minute Oscar Highlights?” Because I’m partial to the shot of Spike Lee with lizards crawling all over him.

Robert Smigel: [Laughing] That one is my favorite one. Also, Charlton Heston walking out, which was just a miracle that I found that. I was just scanning the recordings from the 90s. There were some moments that weren’t in the real Oscar recordings, that hadn’t been preserved on the Oscars website. It was like an entire show that someone had downloaded for some reason. Heston got up to leave while Billy Crystal was setting up another award. But yeah, those are those are probably my two favorites.

THS: Where did “Last Minute Oscar Highlights” come from? How did that all come together?

Smigel: Part of it was just wanting to shed a little more light on the song. That was the serious impulse of it. I wrote all the songs for [Leo]. That was the only one that was like a pop song. I thought kids and moms would listen to this and enjoy it. Then, the Oscars hype is so omnipresent. I just had the idea, ‘I wish I could make a video out of this song.’ So we decided, let’s just pretend it was the sixth nominated song. I didn’t even submit it for an Oscar.

For an Oscar, you’re supposed to submit what song you want considered to be judged for best song. [Netflix] told me to just pick one, so we’d have a better chance — which we didn’t [Laughter]. The song we went with was a little more serious. It was one Netflix really loved. “When I Was 10.” The other one that I would have picked is the one where Leo himself was singing to the girl not to cry, which is the funniest song in the movie. This would have been my third choice for that, but for the purpose of the joke, because it was a bouncy pop song, I just imagined that it would be the one that would demand a ridiculous production number, but one that we don’t have the money to properly show. Hence the embarrassing lizard costumes and the karaoke machine.

Tiffany Topol just slowly wheeling it out and cutting to Steven Spielberg and Annette Bening. She’s a very funny actress. She’s super talented. She can sing and dance and is a great songwriter. She’s amazing and has a new album out called Sophmore Effort. It’s great, you should check it out. So I had this swiss army knife of talent — she didn’t just sing the song, she produced it as well. She’s super talented. That’s where it all kind of started from. I told her the idea. She suggested the lizards in tuxedos. Then I was like, one more thing. I wonder if Joey Fatone could be in it. And then miraculously, we had already scheduled the day we were shooting — it was all favors from friends.

We had our brilliant field producer from my old Triumph days, Jake Plunkett, who is now a segment producer for The Late Show With Stephen Colbert, he put the whole thing together for me. My friend Tom Broecker at Saturday Night Live threw us a couple of costumes. Some of the stuff was just very cheap on Amazon. We picked the shoot date… and it just so happened that as I went through Joey Fatone ‘s Instagram account, which is one of the 20 people I follow.

By miracle, Joey Fatone was going to be in New York that day. Because he was doing GMA. On that particular Sunday, he was flying in to do an eat-and-greet, which sounds like something Joey Fatone made up but it was a real. I called him and he was like ‘Fuck yeah, I’ll do it.’ He’s great guy. We had a blast doing it. My friend Robert Ash who used to be an editor on Conan, did a lot of work on it for me.

It’s funny because last year, I was in an independent production called Between the Temples. It was an independent movie, but it had Jason Schwartzman, Carol Kane, and some other great actors. I played a rabbi — I don’t know I pulled it off. Obviously, tons of makeup and prosthetics to make me look Jewish [Laughter]. It was an independent production and we shot the whole thing in like three weeks. An insanely short amount of time. But people were so committed, it was just a beautiful thing to be a part of. Plus, the movie itself turned out great. It was a hit at Sundance. Sometimes the best things turn out that way. You can just feel people really really trying, believing in something stupid.

The idea for the petition came afterward. I was like, I can’t just let this go on the web with no setup. So I enlisted Triumph to be indignant for no good reason about “When It’s Us” being left off the Oscars. It allowed me to get Marc Shaiman, Judd Apatow, and Conan to post humiliating testimonials at Triumph’s behest. All are clearly written by Triumph. “If you don’t believe me, listen to Conan O’Donnell.” Like he still calls him Conan O’Donnell after 30 years.

THS: At this point, I like to think it’s purely out of spite.

Smigel: It’s hard to tell with Triumph. He is very old for a dog, so he might be losing his memory.

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THS: Speaking of Triumph, I also wanted to say congrats on the latest version of Let’s Make A Poop. I saw the video, and it’s hilarious.

Smigel: I’m glad you said that, because I did another interview where they were asking me “How do you feel about platforming Rob Schneider?” and I’m like, ‘Well, if you like comedy and you like Triumph, then it’s going to be very satisfying.’ Anyone on this platform, Triumph’s gonna rip them a new asshole.

THS: When ripping into people as Triumph, do you prefer taking it to people like Rob who can laugh along with the jokes, or is it more exciting when there’s a bit more tension to everything?

Smigel: I have to admit, I’m happier when people are joking and are to take it. I don’t thrive on that kind of attention that the audience sometimes relishes. One of the most uncomfortable ones I ever did was the Michael Jackson trial. Back in 2005. It was like the opposite of the Star Wars fan line, because the people were similarly dressed, just as ridiculously as the Star Wars people. But they were dead serious defenders of Michael. That was most of them. A lot of them had no sense of humor about it. I don’t enjoy those situations. We had to spend an extra day there. We had to wear people down. It was very hot, we were giving people water and lemonade. That’s when we started to break down defenses and make them realize that we’re just comedians.

Some of the people who were okay with it. Some of the ones who were afraid to talk to Triumph on the first day decided, “Yeah, I’m gonna talk” and so it ended up okay. The audience watching loves that kind of tension. I don’t necessarily enjoy that energy. I’s not really in my makeup I enjoy. I like the Star Wars one a lot more, where everybody can laugh at themselves. With Rob, I told him “If you’re gonna do this, I’m not gonna hold back.” He was like, “No, I get it. Understood.” I mean, he’s a comedian. So if anybody’s going to understand that, it’s somebody who does it for a living. So Rob was relatively easy in that regard.

THS: What excited you the most about getting to bring that show format back?

Smigel: You know, I was gonna make it a regular podcast. When we did the first one in 2019, that was supposed to be something I was gonna do regularly, I was gonna do regular shows in Brooklyn. That first one we did with Lawrence O’Donnell and Pete Davidson and Anthony Scaramucci was so funny and successful. And then the pandemic happened and just just killed all my energy. I did a quarantine version by Zoom that I like very much, and that’s still on my YouTube site called “Quarantine Squares.” like Hollywood Squares with nine celebrities. I’ve done a couple of live ones since.

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This one was special because Weird Al. We had this gimmick of pretending that Weird Al had written all these really bad song parodies and then I got other people who were at the festival to join in on the humiliation. It was a really great satisfying moment… It was probably my most enjoyable live show in 20 years, probably since I did my comedy album.

THS: Is there a chance we’ll see more episodes of Let’s Make A Poop in the future?

Smigel: I don’t know if I have the energy to make it a podcast anymore, but I would like to definitely do more live shows at the very least. If they’re good, I’ll put them out for people to see. But I would love to do more live shows. Booking people is always a pain in the neck. I’m kind of a one-man band sometimes. If I have a if I had a team behind me and a real game plan, I’d have probably done it by now. But there’s still time and still possibilities. I have a lot of financial pressure all the time.

I don’t like to complain, but I have family expenses, you know. So I usually gravitate toward writing movies because they just pay a lot more [Laughing]. But I love doing Triumph this way. I love the rapid-fire game show approach. I love it because it’s a new way of doing passive-aggressive kind of insult jokes. The thing I always liked about Triumph most is the manner in which he insults people. I like that he does insults straight out of a roasts. When he’s doing his on-the-site reporting, most of his insults come in the form of passive-aggressive questions, which is the most fun way to insult people.

THS: It’s been almost thirty years of Triumph. What do you think helps make that character and his comedy so enduring?

Smigel: The biggest thing is that puppets don’t crack [Laughter]. His jokes were old from the start, so that helps. He was already like a throwback style of comedy when he started. I think that’s part of it, just the fact that he looks exactly the same. It’s not like it was funny when he was younger and now it’s pathetic. I mean, if you look at me crouching down, it’s pathetic. But that looked pathetic thirty years ago too [Laughing].

THS: I do love the idea of Triumph in a cardigan with reading glasses on at a type writer, Mickey Rooney style.

Smigel: [Laughing] Yeah, we’re just scanning joke submissions. “We already did that one, already did that. I haven’t heard banter like this since I ate a burrito? Come on, we did that one years ago.”

THS: All this talk of Lorne Michaels’ replacement, I think Triumph needs to take that spot.

Smigel: No one’s asked him yet! [Laughter]

Let’s Make A Poop and Last Minute Oscars Highlight: “When It’s Us” are now both on YouTube.