Legendary television personality Larry King passed away on Jan. 23, leaving behind a legacy in broadcasting and television. 

King began his career in broadcasting in the '50s, working as a radio DJ, newscaster, and sportscaster. He started broadcasting his own radio show, The Larry King Show, in 1978, in which he would interview guests and answer calls from listeners. He then adapted his interview platform to the modern entertainment landscape, beginning his television show, Larry King Live with CNN in 1985. He went on to establish a web series, Larry King Now, in 2012, continuing to remain relevant over many decades.

King's accolades include an Emmy, two Peabodys, and ten Cable ACE Awards. He was inducted into both the National Radio Hall of Fame and the Broadcasters' Hall of Fame in 1989 and 1996 respectively.

Over the course of his nearly lifelong career, King interviewed over 50,000 individuals, ranging from movie stars and singers to politicians and world leaders. King’s interview style was unparalleled: His approach was always warm and welcoming, and he was clearly genuine in his desire to hear what others had to say. It’s fascinating to watch how quickly and easily interviewees opened up to him, as if he were a friend they’d known their whole lives.  

As a tribute to Larry King, here are some of his funniest, most wholesome, and most impactful moments as a television personality and interviewer.

Frank Sinatra (1988)

Though an iconic singer and actor, Sinatra was notorious for shying away from interviews—this Larry King Live chat was his final major interview appearance. Instead of delving straight into Sinatra's career, King and Sinatra began by reflecting on the attitudes of interviewers, which were often off–putting and made Sinatra uncomfortable. They then shifted to a candid discussion about “pimps and whores,” Sinatra's definition of "kiss and tell" writers. During the interview, Sinatra even confessed that he never truly got over his stage fright.

Marlon Brando (1994)

Brando, while promoting his memoir Songs My Mother Taught Me, chose King's show to be his sole interview. The episode was filmed in Brando’s own home, where he was unmistakably comfortable—even appearing barefoot in his recliner. After talking about his childhood and singing a short duet with King, Brando planted a kiss on King’s lips. 

Bill Clinton (1994)

King cited Clinton as his favorite presidential interview, because of how articulate and knowledgeable he was, adding that "He knew the vice president of Zimbabwe.” Speaking of interviewing presidents, King interviewed every sitting president from Ford to Obama—and even Trump a handful of times before he was inaugurated. Through King's casual approach, he made America's leaders seem grounded and human, stating that they "put their pants on one leg at a time,” just like the rest of us.

O.J. Simpson (1995)

King controversially answered a phone call from O.J. Simpson days after his acquittal, during an interview with Simpson’s lawyer, Johnnie Cochran. Whether or not viewers agreed with his decision to take the call, King's willingness to hear Simpson out proved that he was always fair and valued hearing all perspectives.

Nelson Mandela (2000)

King interviewed the former president of South Africa about his release from prison after 27 years. Mandela was a leading figure in the struggle against apartheid, and his reflection of what it felt like to regain his freedom and be elected leader of the people he had spent his life championing was incredibly moving.

Paul McCartney (2001)

Though King later did a Beatles reunion interview with Paul McCartney, Ringo Starr, and the spouses of John Lennon and George Harrison, his solo interview with McCartney stands out. The two legends shared a heart–to–heart while talking about McCartney's grief over the death of Lennon. 

Paris Hilton (2007)

Following her release from jail, Hilton chose to appear on Larry King Live to talk about her “new outlook on life.” Though not many took Hilton seriously, considering her ditzy persona and the fact that she spent a mere 45 days incarcerated, King was nothing but warm and respectful toward her.

Lady Gaga (2010)

This interview stands out because the unpredictable fashionista dressed just like King for the interview. Gaga adorably sported his classic shirt and suspenders look, with slicked back hair and sunglasses. When she asked if she could call him "King Larry," he humbly refused the honor and opted for Larry and Gaga instead.

Snoop Dogg (2013)

Over the years, Snoop Dogg and King built an unlikely yet unbreakable friendship. During their multiple media appearances together, Snoop Dogg taught King how to rap, discussed why marijuana is part of his creative process, and even allowed King to test drive his ‘67 Pontiac.

DJ Khaled (2014)

DJ Khaled is known for having a loud personality, but his conversation with King was calm and profound. The two discussed serious topics like religion and the Middle Eastern conflict, bringing their perspectives as a Jew and a Palestinian sitting at a table together. During the interview, DJ Khaled proudly stated that his goal is to promote peace.

There was never a dull moment in a Larry King interview. His laid–back nature and insightful questions were the perfect recipe for a grand time, no matter whom he spoke with. He is an icon that will be greatly missed.