Flamboyant ex-NBA star Dennis Rodman has arrived in North Korea on a mission of "basketball diplomacy".
The American is running basketball camps for children and will play a demonstration game that he hopes the country's leader, Kim Jong-Un, will attend.
Rodman, who is known for his piercings and tattoos as well as his on-court skills, will have his trip recorded for a show on US network HBO.
Members of the famous Harlem Globetrotters basketball team are accompanying Rodman and will be showing off some of their ball tricks.
The trip comes after the communist state's recent nuclear test, which was condemned around the world, and a month after Google chairman Eric Schmidt visited the country.
Rodman, 51, most famously played for the Chicago Bulls, winning five championships during his career and is considered one of the sport's best defensive players.
The occasional cross-dresser also appeared on Celebrity Big Brother in the UK in 2006, and has said he does not plan to leave behind any of his piercings for the trip.
Shane Smith, the host of the upcoming TV series, admitted the trip was unconventional.
"These channels of cultural communication might appear untraditional," said.
"But we think it's important just to keep the lines open. And if Washington isn't going to send their generals then we'll send our Globetrotters."
The US State Department does not vet private travel to North Korea, but urges Americans travelling there to read a travel warning on its website.
Basketball is extremely popular in the secretive country and its previous leader, Kim Jong-Il, was also said to have been an NBA fan.
During a historic visit by former US secretary of state Madeleine Albright in 2000, he was given a basketball signed by Michael Jordan - one of the game's greatest players.