The Manhattan-born only child of Communist union organizers, and American guerilla poster artist whose gnarled, grotesque depictions of U.S. political figures are immediately recognizable and have been printed and plastered across America – from the Iran-Contra affair and the Lewinsky scandal to Bush’s Iraq War and beyond, including today’s most controversial characters – plumbs his own psychological depths only to discover what makes him love work and life.
What historical art figure would you like to have lunch with? Nancy Spero and Leon Golub are my art mom and dad. He was probably the greatest political painter of his generation and Nancy was the greatest feminist artist. They’re not my teachers, but they helped me more than anybody with my art. I was teaching at the University of Connecticut and got Leon to come up and give a talk there, and every time he saw me, he would say, ‘Let me see your work. What are you doing?’ He’d also say ‘You want to know what I really think?’ and he’d shred it in the nicest way. When I would go to New York – they had a studio on La Guardia Place – they’d take me to dinner.

Betsy De Vos, Learning Swerve, 2018
They were old. He was arthritic and she had her vertebrae in her neck fused and her hands were gnarly. He was a scary looking dude, but they were the greatest. We’d go to an Italian restaurant around the corner and one of my fondest memories is those dinners.Forgive me if I’m not talking about lunch, but I really cherished those dinners with them and I would love to have one more. It would be just a great thrill for me to sit down with them and have mediocre pasta Bolognese.

Donald. J. Trump, Bully Culprit, 2016
What did you purchase with the proceeds from your first sale? Okay, it was 1987 or maybe early 1988 and the first legitimate show I had in L.A. was at Robert Berman’s. I had had a studio in East L.A. that I sublet to a supposed photographer who was doing short time for drug dealing. When I was there, in East L.A., there was this Mexican restaurant, La Posta, and they had the greatest chicharrones in red sauce, deep fried pork skin. I think what I did was we sold one of the Men with No Lips paintings – they’re just little black and white oil paintings – ugly little suckers. I went with my friend Jonathan Salk – he’s a pediatric psychiatrist and it’s always good to have your shrink with you – we went and feasted on chicharrones in red sauce. I treated.
What words or phrases do you overuse? ‘How’s that working for you?’ is one that I overuse, usually when I disagree with somebody. If they say, ‘I voted for Trump,’ I say, ‘How’s that working for you?’ and scream an invective back. But I can’t help myself. I also say things like ‘It’s a long story,’ which it is, because if I’m telling it, it is.

Freedom From Choice billboard on Pico & Robertson, 1991
How do you know when a work is finished? I never know. That’s haunted me. I’ve fucked up more paintings by over-painting them than I care to admit. But actually, my friend Jonathan Salk’s youngest son was an intern for my studio. He went to Wildwood and they had a program where kids would intern with different creative people. I got him. He must have been 15 or 16. He’s in my studio and I was working on a commission, a big charcoal drawing of Hemingway.
Just so we don’t get confused with my positive work, I was also working on John Boehner – Wealth Care -and the intern was in my studio with me every afternoon after school. At one point I’m working on the painting and he says, ‘It’s done.’ He’s a 16-year old kid. ‘What do you mean?’ I said. ‘That’s it. You’re going to fuck it up.’ He was right. After that, I really paid attention to my optimum effectiveness for each image. Maybe I can’t improve this. Maybe this is as good as it’s going to get. Or maybe this is enough and anything else would be too much and take away from the freshness. There is one thing about drawings as opposed to painting – they have a certain kind of life. It’s tracking an artist’s thought process that finished art doesn’t have. Sometimes you feel you have to kill a work of art to finish it – that ain’t true.

George H. W. Bush, It Can’t Happen Here, 1988
When and where were you happiest? Right now. Here’s something for you. Francis Bacon, one of my favorite painters of awfulness – I saw an interview with him and Melvin Bragg – and Bacon says, ‘I’m an optimist.’ Bragg, knowing his work says, ‘Francis, how could you be an optimist?’ ‘Well, I am. I’m optimistic about absolutely nothing.’ Bragg says, ‘How can you be optimistic about absolutely nothing?’ He says, ‘Well, I can.’ And then he explains it. He was just drunk enough. Sometimes if he’s not drunk enough, he won’t tell the truth. If he’s too drunk, it’s messy. But he was just drunk enough and explained himself. What he said was, ‘There is absolutely nothing but you and me right here, right now, and we’re having a good time, so I’m optimistic about that. Now. That’s all there is.’ And also [I’m happiest] when I’m not painting!

Donald Trump, Jr., Falsetto, 2018
What is your most treasured possession? Oh, god. My parents didn’t believe in private property, since they were Communists, and they went to Fire Island ever since I was zero until I was nine and went to baseball camp. It’s very valuable property now and they had a chance to buy beach cottages for $3,000. and they never would. The two things that screwed me completely in our capitalist cultural economy were those parents and LSD. After experiencing the two of those things, I’m not really into possessing. I have some stuff. I like stuff, but I don’t have the real entrepreneurial drive that would be very helpful for my so-called career. I also don’t have the urge to collect stuff. There’s stuff that means something to me because it evokes a relationship with another person – or something like that – as a fetish object. I really demur when it comes to my possessions. I’m grateful to possess my faculties. It’s great to have a wonderful wife and a relationship with her, but I don’t feel like I possess her or anything. That would be a big mistake.

John Bolton, Used War Salesman, 2018
Where is your ideal escape destination? That’s a good question, considering I might have to leave America. I like [where I live] here in Los Osos. It is an escape in a way for me, although I like Italy a lot. Italians are really nice. Every time we go to Italy, I don’t know how this happens, but Italians have this sense that I am their personal clown from America. They’re so interested and so curious. We were in Florence. We got there at 11pm on a Sunday night. It’s dark, kind of cold. We say to this concierge in this hotel, ‘Where’s a place we can go eat? We’re starving.’ He says, ‘Go up the street.’ We go up the street. It’s dark. We look into this restaurant and it’s completely packed – no room.

Kellyanne Conway, Knows Job, 2017
We go up the street farther and there’s a restaurant. It’s packed, but there’s a table or two. It’s a mom and pop place and this middle-aged beautiful woman seats us. We’re the only Americans in the place. By then it’s midnight on Sunday night. ‘What are you going to have?’ I saw something that looked like maybe it was clams – vongole. ‘I’ll have that.’ ‘Oh you want vongoles?’ And all the people start applauding. Everywhere we went in Italy – people would start talking to me and laughing at me. How did they know? I didn’t even have my floppy shoes and red nose on.
What’s the worst survival job you’ve ever had? Artists are famous for the shit jobs they’ve had. This is – or it was – in the olden days, my generation and before, a shit job was a rite of passage for any person who was foolish enough to think art was a profession. I’m not going to say it’s the worst job, and I can’t believe I came out of it alive, but in 1970, I drove the graveyard shift for Yellow Cab in San Francisco. It was right after the Zodiac Killer had killed a graveyard Yellow Cab driver in his cab, so they couldn’t hire anybody except ex-cons and me. It was me and a bunch of ex-cons running wild. One of the guys was Toxic Bob. He’d just got out of the joint – San Quentin – for blowing up his parents’ house with his meth lab in the basement.

The Second Scumming, 2001
You’d get one day or night off a week. That’s when he made new meth. These mad men were driving around in the middle of the night whacked out on Bob’s home-made meth, not paying attention to lights and refusing to pick anybody up, because there was no percentage. They all had a scam. They wouldn’t pick anybody up because they were running drug dealers around town. I lasted a year. That year and this year – because of Trump – that year because of Toxic Bob and the boys. It was wild, actually it was really insane. That was one of my survival jobs that I barely survived.

Jim and Tammy Faye Bakker, False Profit, 1988
What TV series from your youth best describes your approach to life? My mother’s favorite show was Rawhide – she whistled the theme, and The Sid Caesar Show – Your Show of Shows. That was family entertainment. The three of us and the cats – we’d all watch together. Sid Caesar and Imogene Coca – that was great. I just loved that show. Not that I understood anything, but it didn’t matter. It got into my kishkas, in my bones, and it was wonderful to see a female comedienne. She was terrific. My parents had a great sense of humor and humor got weaponized for me very early.

Bill Clinton, Dough Nation, 1997
If you could change one thing about yourself, what would it be? I’d say I’d like to be less judgmental when first meeting people. Plus, I grew up in Manhattan, and whether you like it or not, as soon as you go outside or on the subway, you’re in contact with thousands of people every day. Maybe it’s a survival mechanism, but you have to make snap judgments about them – like an animal. Can I eat them or are they gonna eat me? I’ m a really practiced surface semiotician. Looking at somebody – and everything you wear – is you. When people say where you from and you say Los Angeles, they think you’re superficial. That we’re deeply superficial. But in New York, it’s different but it’s the same. You’re making snap judgments when you’re looking at people for the first time.

Jesse Helms, Artificial Art Official, 1990
If someone’s wearing Nikes, everything’s a signifier as to who they are. What kind of cell phone do you have? What kind of car do you drive? I do that too fast. I gotta slow down a little bit. I love people, so it’s not fair. I’d rather ask them 20 questions and get to know them than just go, ‘Oh, you’re wearing rhinestone glasses…’
What is your most treasured memory? Meeting [my wife] Debbie. It is a significant moment because it has values attached to it. I got talked into going to a meeting at Tony Bill’s screening room at 73 Market Street by Joan Hyler who was a Vice President at William Morris. She called and said that the Christic Institute was bringing a lawsuit against 29 individuals [including] Oliver North, and couldn’t get any traction in the major media. They needed money and aside from that they needed educational materials. I’d only done about five posters at that time and nobody knew it was me. Joan invited me because she knew they would need a poster. I went to this meeting with the woman I was living with at the time, an art historian who didn’t really want to go at all.

Contra Cocaine, 1988
The event had already started. It was a presentation in the theater. It was dark and people were onstage and the usher took us to the only seats available, which were next to Debbie – she’s a graphic designer – and her graphic designer boyfriend. I said, ‘I’m Robbie Conal,’ and Debbie says, ‘You’re not him.’ ‘And you are absolutely gorgeous,’ I’m thinking, ‘and I’m in big trouble.’ I turned into Ralph Kramden. But that’s how we met, which was great, and then we were put on the poster committee together. We did Contra Cocaine, the poster after Contra Diction. We got to know each other after that. She saved my life, among other things. That was a great moment, the ‘You’re not him’ moment. I cherish it, and she says that it didn’t happen, but it did.

Ronald Reagan, Contra Diction, 1988
What makes you smile? Waking up in the morning makes me smile. Like, ‘Ooh, I’ve got another day.’ This is great. I love people. Really.
What makes you cry? The same thing – people.
What is your go-to drink when you toast to a sale? An Arnold Palmer. I don’t drink. Been there, done that.
After an all-nighter, what’s your breakfast of champions? Postering is night work, so my breakfast – there’s only one kind of bread that I will eat and that’s from Superba Bakery in Venice. I import it to Los Osos. It’s their basic sourdough bread and my thing is a toasted slice of that bread, English marmalade and Santa Cruz peanut butter, creamy. If you’re gonna eat peanut butter, it has to be Valencia peanuts – and maybe a banana. We have a Coffee Roaster and they roast this great Vienna dark roast beans. So, a cup of that coffee with dark brown sugar, half and half and my PB and J.

Paul Manafort, Russian Undressing, 2018
Who inspires you? Alexandria Ocasio-Cortez. She inspires me. Wonderful people inspire me. All animals great and small inspire me. I draw cats, and I’m not kidding around. Cat portraits are soul-melding, and as an antidote to what I do most of the time, I’ll do cat portraits.
What’s your best quality? Hopefully, no people will disagree with me about this, but I think it’s my sense of humor. My counter-punching sense of humor. Repartee. You say something and I say something back. That’s the best I can do. Back and forth. Back and forth. A lot of people don’t like that, but then there’s people who wonder what the hell is he talking about.
What’s your biggest flaw? Some people might say my sense of humor.

Ivanka Trump, Branding Irony, 2017
What is your current state of mind? Desperate optimism.
What do you consider your greatest achievement? Finally finding what I was put here to do. I’m a late bloomer in that regard, but I actually – here’s the thing – what I figure the best we can do is apply what you do best to what you care about most. For myself, I kind of figured that out. It took me a long time, and I’m not saying I’m as good as I can be at it, but that is what’s made me at least a whole person. Take it or leave it. That’s really true. Painting is one thing, painting about making art about social and political issues is another. It’s fraught and not easy to do well – trying to tell people what to think, propaganda. [And] I don’t believe in telling people what to think. In fact, it’s hubris. Especially for an artist. I so try to avoid propaganda! Also, just showing your work to a few people in an art gallery isn’t enough either for me, so putting the two sides of my personality together.

Sarah Huckabee Sanders, A Twist of Fake, 2018
If you’re making art about public issues that you really care about without figuring a way to distribute it to the public doesn’t work. Making art about stuff I really care about and figuring out a way to distribute it as best I can, which isn’t so great, is the best I can do. Regular American public people really cured me. I couldn’t do one without the other. Just making the art wasn’t enough; just putting stuff up on the streets wasn’t enough. Putting goofy stuff on the streets at best gets to tickle them into thinking along with me – that I care about democracy with a small ‘d.’ That’s the best I can do for myself.

Gen. Mike Flynn, Fire Away, 2018
If you were to die and come back as a person or thing, what would it be? I’d probably be a dinosaur, I don’t know. A cat would be good.

Robbie Conal postering; photo by Sean Meredith
Cover image by Sean Meredith; all other photos by Alan Shaffer, except where noted
Follow the artist on Instagram or reach him at robbieconal.com