Former National Basketball Association (NBA) star Dennis Rodman, seen as a master of "basketball diplomacy", is expected to meet North Korean leader Kim Jong Un again after his arrival in the North on June 13. This is at least his sixth trip there, having made three visits to the reclusive country in 2013.
Rodman, considered one of the best defensive players and rebounders in NBA history, first visited North Korea in 2013 along with members of the Harlem Globetrotters basketball team and a film crew from Vice magazine.
During that trip, he sat next to Kim as the duo watched a basketball game, after which Rodman told the audience that Kim had "a friend for life" in him.
Kim, who was educated in Switzerland, is known to be an avid basketball fan - in particular of the Chicago Bulls, which Rodman played for in the 1990s.
Rodman has spent time with Kim's family, and even publicly sang "happy birthday" to Kim on one occasion.
In an interview with Dujour magazine about his friendship with Kim, Rodman said: "That little kid is changing North Korea for the better, and once we see that, maybe he'll just loosen up and start opening the door for the people of the world."
Here are other stars who have cultivated some kind of relationships with famous leaders or their family:
1. STEVEN SEAGAL AND VLADIMIR PUTIN
The relationship between action movie star Steven Seagal and Russian President Vladimir Putin is one that is sizzling with testosterone.
Seagal, the star of action hits such as Above The Law, Under Siege and Hard to Kill, has also worked as a bodyguard and martial arts instructor, most notably to James Bond actor Sean Connery.
Putin himself is no stranger to macho theatrics, having been filmed shooting a tiger with a tranquiliser dart, flying in a hang glider and riding a horse shirtless.
In addition to sharing the same birth year, both men have black belts in Japanese martial arts.
In a 2013 interview with Russian television, Seagal said that he had wanted to get to know Putin better after being "impressed" by a life-size statue of the founder of Judo, the first time he stepped into Putin's house.
In the same interview, Seagal called Putin "one of the greatest world leaders, if not the greatest world leader alive today... he's not afraid to stand up and do what needs to be done".
In 2014, Seagal was reported in Russian state-run newspaper Rossiskaya Gazeta as expressing support for Russia's controversial annexation of Crimea , calling Russia's actions "very reasonable".
The Guardian reported that Putin personally presented Seagal with a Russian passport at a televised meeting at the Kremlin in 2016, saying he congratulated Seagal and that he hoped their "personal relationship will remain and continue".
2. MICHAEL JACKSON AND PRINCE ABDULLAH AL-KHALIFA
Four years before his death in 2009, "King of Pop" Michael Jackson was embroiled in legal troubles and a scandal. However, he found help in an unexpected ally: The Prince of Bahrain, Abdullah Al-Khalifa.
According to the New York Daily News, Al-Khalifa had a "close personal relationship" with Jackson, after Al-Khalifa had reached out to Jackson with financial support while the latter was on trial for child-molestation charges.
In addition to paying for Jackson's multi-million dollar legal fees, Al-Khalifa also reportedly paid US$350,000 (S$484,435) for Jackson to take a trip to Europe, as well as US$300,000 for a "motivational guru" for Jackson.
Later in 2005, Jackson also travelled to Bahrain as a guest of the royal family.
A BBC report quoted an anonymous Bahraini official as calling Jackson "a long time friend of the (royal) family".
In 2008, however, their friendship appeared to break down as Al-Khalifa sued Jackson for US$7 million, claiming that the singer had failed to produce recordings, a book and a musical for him.
The case was settled out of court later that year.
3. BEYONCE, USHER, MARIAH CAREY, AND THE GADDAFIS
Singer Beyonce Knowles is well-known for her history of activism, and has become a rallying symbol for feminists and other activists around the world.
In 2009, however, along with fellow pop stars Mariah Carey and Usher, Knowles reportedly gave a private New Year's Eve performance at a party thrown by Hannibal Gadaffi, the fifth son of now-deposed Libyan dictator Muammar Gaddafi.
Various online sources claimed that the singers were paid US$1 million to US$2 million each for the performance.
The stars' appearances drew flak at the time as Hannibal Gadaffi had just a week before been accused of allegedly beating his wife, while Muammar Gaddafi was rumoured to be behind the bombing of Pan AM flight 103, which killed 270 people in 1988.
Carey afterwards offered a statement of apology on her website, saying that she felt "horrible and embarrassed to have participated in this mess... We need to be more aware and take more responsibility regardless of who books our shows."