When Shepard Fairey was a young man he gave his parents an ultimatum: let me go to art school or watch me flame out in college. Art school won.

“When we were arguing about it, I sort of bluffed and said, ‘Well, if you force me to go to liberal arts college, I’ll fail out and that’ll be more embarrassing than telling your friends that I get A’s finger painting,’” Fairey recalls.

That anecdote hints at the hard-nosed rebelliousness that has characterized Fairey throughout his career as street artist, creator of Andre the Giant “Obey” iconography and designer of the Obama “Hope” poster that defined a candidate and a presidency. The full range of his exploits—the political highs and the legal lows—are on display in the Hulu documentary Obey Giant, directed by Oscar-winning filmmaker James Moll, that is now in contention for Emmy consideration.

Don Holtz/Allentown Productions/Hulu

The film traces Fairey’s ascent as a cultural force from his early days in South Carolina, which he describes as suffocatingly conformist. After his showdown with his parents he attended the Rhode Island School of Design, where he overlapped with fellow student Seth MacFarlane (he says they didn’t know each other well at RISD but appreciates that MacFarlane later name-checked, or rather art-checked him in an episode of Family Guy).

“[Seth] was a similar kind of person with a mischievous streak and a little bit of defiance towards authority,” Fairey notes.

While teaching a friend to stencil he seized on an image of the massive wrestler Andre the Giant and later began pasting a modified version of the artwork at points all around Providence and Boston. In a foreshadowing of his influence on political campaigns, he slapped the head of Andre the Giant onto a billboard for Providence mayoral candidate Buddy Cianci in the early ’90s. That act triggered an avalanche of attention from locals who puzzled over what kind of message the altered billboard was intended to send.

“It was so amazing to see all the different takes on why I did it, and what the commentary was,” Fairey tells Deadline. “It was like a Rorschach test on steroids.”

Don Holtz/Allentown Productions/Hulu

There was always a political dimension to his work because by illegally papering it on walls, street signs and other structures he was declaring that public space belonged to artists, and the people, as much as government or corporate entities.

“I tried to integrate my work into the cityscape in a way that I didn’t think was destructive,” he asserts. “People are always going to have their different takes on what is and what isn’t destructive. Rule breaking, even if it’s harmless rule breaking, is threatening to people who love rules, and there are a lot of those people.”

He later used his artistic talents to protest President George W. Bush and his military intervention in Iraq.

“I have to make work that’s a counter-narrative” to Bush’s ideology, he explains in Obey Giant.

But it wasn’t until presidential candidate Barack Obama came along that he found something to be actively “for” instead of against. Independently from the Obama campaign, but with its knowledge and assent, he created the iconic Obama “Hope” image, basing it on a news photograph snapped at a public event attended by the then junior senator from Illinois.

Jon Furlong/Obey Giant Art

A key sequence in the documentary follows the artist’s high with the Obama poster, which helped get the candidate elected, to the soul-crushing low of being dragged through a legal ordeal by the Associated Press, which sued Fairey after discovering it was an AP photo that had served as the basis for his “Hope” image.

“I think they were so overzealous about the idea that they could take an image that became famous and make a deterrent bullying case with it,” declares Fairey, “that everyone would see and then [realize], ‘Oh, my god. You used an AP photo, you get the death penalty.’”

Eventually the case was settled out of court, which meant there never was a legal determination of whether Fairey’s poster qualified as a “fair use” exemption under copyright law.

“It was a learning experience for me and I do respect photographers,” Fairey insists. “In the cases where it’s possible, I want to collaborate with photographers and compensate photographers, but there are instances of political art where neither the subject, nor the photographer, is going to be excited because they don’t agree with the political viewpoint.”

The bruising experience with the AP may have left Fairey somewhat chastened, but it hasn’t deterred him from making street art—which has landed him in jail on vandalism charges on numerous occasions.

Jon Furlong/Obey Giant Art

In the Trump era he has designed posters that affirm the dignity of Latinos and Muslims, and protest the administration’s immigration policies.

“I did the screen images for the Woman’s March/Alternative Inauguration in 2017,” Fairey comments. “They were really about celebrating the diversity and undeniable humanity—rather than looking at people fearfully, let’s look at them as another human being first, giving them the benefit of the doubt, and recognizing beauty in people who don’t look like you, have the same religion, etc.”

He has created a single explicitly anti-Trump poster, an unflattering image of the president’s mouth, that was made for the band Franz Ferdinand for their song “Demagogue.” Fairey says he has no current plans to do more.

“I think that Trump’s such a narcissist, he just loves to be referenced,” he says. “I’m not going to give that to him.”