Jelly Roll is undoubtedly on a hot streak. After toiling on the edges of the industry for nearly a decade, his career has gone supernova over the past year thanks to his singles “Son of a Sinner,” “Need a Favor” and “Save Me,” the latter of which earned him a Grammy nomination. He rolled across the United States on his 44-city Backroad Baptism Tour in 2023, has played a string of festivals this year and is slated to hit a few more this summer, along with hopping on shows with Morgan Wallen and headlining this fall’s Beautifully Broken tour with Warren Zeiders and Alexandra Kay.

But if you look at Jelly’s road history one thing you’ll notice is that his gigs have kept him within the lower 48, a situation he explained while talking to Jon Bon Jovi for Interview Magazine earlier this year. During the chat, the 39-year-old singer born Jason DeFord noted that his felonious past has kept him grounded when it comes to playing gigs overseas.

“It’s funny, America has finally agreed to let me leave and give me a passport, but some countries won’t let me come because of my felonies,” he told Bon Jovi. “We’re working on that. I think it’s going to work in my favor.” Then, on Howard Stern‘s SiriusXM show Wednesday morning (June 12) after the host asked if Jelly’s past misdeeds are still keeping him grounded, the singer said, “I actually got off the phone with a lawyer yesterday, We are working… it’s getting good, it’s starting to look promising. It didn’t look good even just six months ago, but it’s starting to look really promising.”

Jelly Roll has spoken openly about his past scuffles with the law and his jail time, including dozens of stints behind bars on drug charges going back to when he was 14, as well as an arrest at 16 for aggravated robbery that landed him a year in prison when he was tried as an adult; he had been facing a potential 20-year sentence in the case, though he served just over a year behind bars and seven years of probation. He’s also talked about the time in 2008 when, at 23, he was locked up on drug dealing charges when his daughter Bailee was born. Among the repercussions are an inability, until recently, to secure a passport, as well as an inability to vote, volunteer at most nonprofits or own a firearm.

So what’s still keeping him from getting his first passport stamp? Billboard spoke to several prominent European immigration lawyers to find out what the hang-up is and whether Jelly might be able to rock stages overseas in the near future. (The experts agreed to speak in general terms about immigration laws in their country, but had no first-hand knowledge of Jelly Roll’s case.)

First, the good news.

According to the rules about entrance to the 26 European countries that allow unrestricted travel within their borders — collectively known as the Schengen Area, which includes Austria, Denmark, Finland, France, Germany, Greece, Italy, the Netherlands, Poland, Spain and Sweden, among others — non-EU nationals can be denied entry if they are considered a “threat to public policy, internal security, public health or the international relations of any EU or Schengen country.”

A prominent Italian immigration lawyer who requested anonymity tells Billboard that once you legally enter a country in the Schengen region, you are free to travel among the countries with a valid passport, as long as you are not listed on INTERPOL’s list of restricted individuals. The region does have a list of serious criminal offenses over the previous decade — or 20 years in the case of terror offenses — that an applicant for entry must report before visiting. The list of barring offenses includes terrorism, human trafficking, child pornography, drug/weapon trafficking, fraud, money laundering, environmental crimes, murder, racketeering, arson and nuclear material trafficking.

Based on that list, Jelly Roll’s priors do not appear to rise to the level that would bar him from visiting the Schengen countries. The attorney noted, however, that those rules are slated to change in 2025 when non-EU nationals who don’t need a visa to travel to the Schengen area — a list that includes U.S. citizens — will have to apply for travel authorization through the ETIAS travel portal for short-term (90-180 day) stays; at present, if you have a valid passport and don’t plan to stay for more than three months a visa is not required to enter the region.

At press time, a spokesperson for Jelly Roll had not returned Billboard‘s request for comment on the status of Jelly’s overseas touring plans.

The bad news, according to Matthew James of leading U.K. immigration law firm Bates Wells, is that the United Kingdom has what are called “General Grounds For Refusal” laws that look at whether an individual has previously overstayed their visa in the country as well as a past history of criminality. What gets captured under that rather broad umbrella are mandatory and discretionary grounds for refusal, which James says are somewhat “opaque.”

“If you’ve received a custodial sentence of more than 12 months, that should be a bar to entering the U.K., so there’s absolutely no chance of you coming in if you’ve done 12 months of jail time,” he says, noting that if you’ve done less than 12 months but are a “persistent offender” with multiple drug offenses you can be refused as a “persistent” offender; you can also be refused if the offense has caused serious harm.

However, for artists looking to visit for less than six months to stage a series of performances, there is an added wrinkle that if they’ve received a conviction within 12 months of their visit, their application will also be refused, which should not apply to Jelly Roll since his convictions occurred more than 20 years ago.

The U.K.’s secretary of state could also decide that an individual’s presence in the nation is “not conducive to the public good” because of their character or other reasons, with James pointing to Tyler, the Creator announcing that his lyrical content had gotten him banned from entering the United Kingdom for 3 to 5 years due to his then-violent and misogynistic lyrics. At the time, the Home Office issued a statement reading, “Coming to the U.K. is a privilege, and we expect those who come here to respect our shared values. The Home Secretary has the power to exclude an individual if she considers that his or her presence in the U.K. is not conducive to the public good or if their exclusion is justified on public policy grounds.” Tyler has subsequently been invited to the nation with no incident.

Snoop Dogg has talked about how the late Queen Elizabeth II helped him avoid getting booted from England in 1994 when he was facing first- and second-degree murder charges for which he was later acquitted. Ja Rule said he was “devastated” when his planned 2024 U.K. tour was canceled after he was denied entry due to his criminal record on gun possession and tax evasion.

James says that, in general, American visitors — especially those coming for permitted paid engagements — can enter the United Kingdom for what are called “permit-free” festivals, such as Glastonbury, without applying for a visa. In a testament to money talking, he added that the ultimate discretion lies with the secretary of state. “If you are a Snoop Dogg and you are about to sell out Wembley Stadium for three nights and it’s going to make a huge amount of money for the U.K. economy and he’s done loads of great work rehabilitating other people and people learning from his errors and never caused another issue since in 20-plus years,” says James, you could likely talk to someone more senior in the government and get some leeway on the rules, which, he notes, are mainly intended to bar known criminals from living in the country.

That said, those who have committed particularly heinous crimes face a different standard. R. Kelly — who is currently serving a 20-year prison sentence on child sex abuse convictions — is unlikely to ever be allowed to perform in the United Kingdom again following his release.

Jelly Roll has talked extensively about the work he’s done talking to youth about his law-breaking days and visiting facilities to share his story, including donating a recording studio to the Davidson County Juvenile Detention Center, where he was incarcerated as a teen, in 2023.

James says that given that Jelly Roll’s arrests and incarcerations occurred mostly when he was young, that he’s clearly worked on rehabilitating himself and that he’s on the upswing of his career, it’s always possible that “overarching discretion” could come into play. This allows officials not to apply the rules in the strictest manner, particularly if an artist’s concerts will bring significant revenue to the United Kingdom and the person is not a perceived risk. “They will fly in on their private plane and play their set at Wembley and then leave,” he says. “They would have to show remorse and a redeemed character and the benefits to society they are bringing and the economic advantages they’re bringing.”