Brandon Duncan has been making music as Tiny Doo since the early 2000s, but his music didn’t attract a lot of attention until last year. His mixtape “No Safety” found an audience he probably did not expect: San Diego law enforcement. The album features a gun on the cover and lyrics like, “ain’t no safety on this pistol I’m holding,” both tropes common in gangsta rap. But the album has placed Duncan in an unusual legal bind. He has been charged with nine counts of “gang conspiracy” related to a series of shootings allegedly committed by the Lincoln Park Bloods gang between May and July 2013. If convicted, he will face twenty-five years to life in prison.

Duncan has never shot anyone, and prosecutors are not alleging that Duncan directly participated in the shootings themselves. Prosecutors linked Duncan to the other defendants, several of whom are also charged with attempted murder or “shooting at an inhabited occupied structure,” based on a mixtape he released a year after the shootings occurred, a couple of dated social media photos with a single documented gang member, and a 17-year-old police report documenting Duncan as a member of the Lincoln Park Bloods. If the court finds the gang responsible for the shootings, the court may go on to find that Duncan “promoted” and “benefited from felonious conduct” under the STEP Act by making music.

California voters passed the Street Terrorism and Prevention Act, or STEP Act, by ballot initiative in 1988. The STEP Act provides criminal penalties against anyone who “willfully promotes, furthers, assists or benefits from any felonious conduct” by gang members. What voters likely did not realize in passing the law is that it might be used to sweep anyone who had any ties to a gang—sometimes, ties so tenuous that defendants wouldn’t know they had them—behind bars.

Since the law’s enactment, more than two dozen cases have been brought alleging “gang conspiracy” as the act defines the term. In many of these, such as 2013’s People v. Johnson, the charges also include actual violence. Duncan’s case is the first in which prosecutors have alleged that the rap lyrics and a couple of Facebook photos alone are sufficient to connect a defendant to a “gang conspiracy.”

Duncan has never been convicted of any crime. According to police records, he was a member of the Lincoln Park Bloods when he was a teenager in 1997, but Duncan’s beefs with rivals most often took the form of rap battles. He was arrested together with two Bloods members in 2008 on pimping charges, but the charges were dismissed. Duncan says he since given up any gang “fam” for a real one: his seven young kids and his girlfriend.

Duncan grew up in one of the most violent San Diego projects. Of his music, he says, “It’s entertainment. It’s not real.” Duncan has compared himself to Rick Ross, a former corrections officer turned rapper, explaining that his own raps are just telling the stories of urban communities.  In “Fly Away,” he raps about his volatile beginnings and his struggle for a better life: “One day it's the sunshine, next day the rain came, but deep down inside you just playing the blame game.” Other lyrics criticize the gang life, as in “Wicked City,” where he asks, “Crime pays? What the fuck you talking ’bout?”

The bizarre case of Brandon Duncan illustrates what’s at stake in Elonis v. United States, a pending First Amendment case argued before the Supreme Court in December. Elonis raises the question of when words—in Elonis’ case, a series of Facebook posts—become criminal. The justices’ issue is a technical one: crafting the proper standard for determining whether a communicated expression is a “true threat.” Should it be enough to prove that a “reasonable person” would have known the words sounded like a threat, or should the government have to prove beyond a reasonable doubt that this defendant intended them to be a threat?  Lurking behind that issue is the question of who judges the words of marginal figures like Tiny Doo.

Unlike Tiny, Anthony Elonis is not a recording rapper; but after his wife left him, he began posting “rap lyrics” on a Facebook page. They seemed to be threatening to harm his co-workers, his ex-wife, FBI agents, and children at nearby schools.  The judge in the trial instructed the jury to evaluate Elonis’s lyrics by the “reasonable person” standard. He was convicted on four counts of making threatening communications and sentenced to three and a half years in prison.

Nine of the 12 federal courts of appeal have held that threatening speech does not deserve First Amendment protection, regardless of the speaker’s intent. What are the implications for rappers like Tiny Doo, or Eminem? The latter artist shot to fame with The Marshall Mathers LP, which contained several songs expressing fury toward his ex-wife. Several of these, including “Kim,” “Kill You” and “Criminal,” Elonis cited in his brief as the model for his own lyrics. In “97 Bonnie & Clyde,” one of the songs cited in Elonis’ brief, Eminem says:

Da-da made a nice bed for mommy at the bottom of the lake

Here, you wanna help da-da tie a rope around this rock? (Yeah!)

We’ll tie it to her footsie, then we’ll roll her off the dock.

There goes mama, splashin’ in the wa-ta

The tone is very close to some of Elonis’s lyrics, but Eminem has never been charged with a crime based on his lyrics. It’s not because his lyrics are “harmless,” either: After his songs were released, the famous rapper’s wife attempted suicide. At oral argument in Elonis, the government argued that Eminem’s case was different because he “said it at a concert where people are going to be entertained.”

This potential double standard for celebrities and non-celebrities makes police, prosecutors, and judges into arbiters of who is an artist and what is art. Most live in a different world than the rappers they assess. Judges may tolerate a commercially successful rapper’s words. But the more radical messages within the genre—as in other forms of outsider art—may run up against judges who do not understand or approve of the subculture that spawns them. Hip hop is not the first genre to elevate lyrical expressions of revenge. The artistic space in many musical forms is a site of fantasy, in which imagined actions that have no relation to the real world the singer lives in, or the people in it, can be expressed.

Beyond that, the prevalence of “persona rap” cautions against taking lyrics too literally. In persona rap, the rapper takes on an alternate identity. Eminem rode to fame in a car driven by his Slim Shady persona. In “Twin Hype Back,” the DJ Prince Paul, speaking in the voice of Chest Rockwell, asks, “How you feeling now sweetheart? A little more relaxed? Maybe it’s that half a molly I put in your Mountain Dew.” In the song “Bad Bad Daddy” by the hip hop group Atmosphere, MC Slug brags about neglecting his children: “You can find me over there at the bar” and “you ain't even gotta ask I don't know where they are.” These songs don’t prove that Chest is a date rapist, or that Slug is a bad parent, any more than the soliloquies of Hannibal Lecter prove that author Thomas Harris is a serial killer.

Other legal factors complicate Elonis’ case. Before he began posting as the rap persona Tone Dougie, Elonis, as Elonis, posted a series of horrific statements against his ex-wife. Among them was a suggestion that their son “should dress up as matricide for Halloween.” Because of these circumstances, one possible outcome is that Elonis could be retried and convicted even under the stricter standard that judges his subjective intent, and not just whether a reasonable person would find his speech threatening. If the Supreme Court remands the case back to a lower court on those grounds, the business of judging rap lyrics could fall to juries instead of judges.

The publicity hasn’t been entirely negative for Tiny Doo, whose songs have racked up more than 10,000 hits on the audio website Soundcloud since the state indicted him. But might other rappers start scrubbing their lyrics to avoid being threatened with life in prison? The real threat from a case like Tiny Doo’s (and even Anthony Elonis’s) is that the government will chill the expression of inner pain that makes art powerful, whether judges and jailers like it or not.