Credit: Alamy

Biggie Smalls and Howard Marks might be the last two people you’d put together, but the pair allegedly have a strange connection. Brooklyn-born Biggie is considered one of the greatest rappers of all time with hits such as ‘Juicy’ and ‘Big Poppa’ and classic albums in Ready to Die and Life After Death, while Marks was a drug smuggler from Wales. Naturally, their paths don’t add up, but there appears to be a surprising crossover.

Marks (also known as Mr Nice) got his start smuggling cannabis, and from that moment, his life “changed completely.” He said in footage from the Hunting Mr Nice: The Cannabis Kingpin documentary, “I started dealing, buying and selling, initially just to be able to afford to have enough to smoke, which was quite common amongst students.”

Eventually, he went on to run a drug-smuggling operation from Palma, Mallorca in the ’80s while living with his wife and three children. Marks was one of the most prolific smugglers, importing thousands of tonnes of cannabis into the UK and US. In 1988, he was arrested in Spain on trafficking charges and extradited to the US, where he was jailed in 1990 for 25 years. However, in 1995, he was released due to good behaviour.

During an interview with Big Rat TV, Welsh photographer Skin Phillips told a story about Biggie and Marks crossing paths in the US. He claimed that Marks taught the rapper English and drama while behind bars.

“Howard Marks used to call Pancho [from Dirty Sanchez] to go for a pint, they were like bros,” he began. “Imagine that, Pancho and Howard Marks in Glastonbury. Flipping heck. So Panch — this is a great story — Pancho is wearing this Biggie Smalls shirt, right? Howard is looking at him, saying, ‘Biggie Smalls? Who the fucking hell is Biggie Smalls?’ Pancho is like, ‘Biggie Smalls, you know, Big Poppa, Biggie Smalls.'”

He continued, “[Marks is like], ‘Fucking hell, that’s Christopher Wallace.’ And Pancho’s like, ‘How the fuck do you know that’s fucking Christopher Wallace?’ [Marks said], ‘Well, I taught him English literature and drama in Oklahoma Penitentiary,’ I think, can’t remember. ‘He was one of the good ones.’ Drama and literature in jail.”

Biggie was no stranger to the drug world himself, whose day-to-day life before music involved selling drugs on street corners. “I was just on the corner, selling drugs with my n*ggas. I’d wake up around nine o’clock to catch the check-cashing place at 9:15,” he told Interview Magazine in 1994.

“The crackheads get checks from Social Security, and on Saturday they get all their welfare checks. And when they cash those in, they’ll usually want to buy drugs. So we’d be up early—as soon as they get their money, we’re going to be the first people they see.”

He added, “The only time hearing somebody got killed is a surprise to me is when it’s somebody I was close to. Then, I have mourning for them. But just to hear ‘blah-blah got smoked’ is nothing to me. It’s just average shit.”