It may be hard to remember now,  amid all the jokes about his age, multitude of wives and softball questions, but there was a time when Larry King was the biggest star on cable television, period.

That was back when CNN had no competition, as the gravelly-voiced kid from Brooklyn first started doing his radio interview show for television, cozying up to celebrities and newsmakers with an odd charisma that somehow got them to open up a bit.

On Thursday, King will host his last original show for CNN, leaving the channel after 25 years to make way for British tabloid editor-turned reality show judge Piers Morgan, whose hourlong interview show starts next year. I wrote a feature story for Sunday's newspaper about King's history and the roots of his popularity -- going all the way back to his 20 years on radio and TV in Miami and arrest for grand larceny amid accusations he stole from a friend.

But King developed a reputation for fumbling facts in interviews and asking odd questions because he didn't research or prepare for guests. Which made for a lot of uncomfortable moments on air.

As we count down to the king's last show, here's a list of his biggest gaffes and a few video clips.

Larry offends Jerry Seinfeld (2007) – He turned it into a joke, but it was hard to tell whether Jerry Seinfeld was truly irritated when King asked whether NBC canceled his popular sitcom, which the comic ended by his own choice at the show’s height in 1998.

Larry goes eating and driving with Snoop Dogg (2008, 2010)– Hard to tell what’s worse; watching a 70-something guy who has had a quintuple bypass sit down to a plate of fried chicken and waffles with one of rap’s most profane rhymers in 2008, or seeing the host chided by Snoop two years later for missing a turn while using his patented GPS voice samples. Like watching your grandma trying to freestyle.

Marlon Brando kisses Larry and more (1994, 1996) – At the end of a supremely odd 1994 interview where the overweight acting icon held forth barefoot, put on red suspenders and sang, Brando eventually kissed King goodbye on the lips. In an interview two years later, he’d tell King Jewish people controlled Hollywood and allowed stereotypes about every other minority group. Curiously, King still cites the first interview as one of his landmark “gets.”

Larry confuses the guys from Friends (1997) – Never a pop culture expert, King mistakenly called actor David Schwimmer Richard and Matthew Perry’s character Chandler by the name Charles during a 1997 interview with the cast of Friends during the height of their popularity (for the kids, imagine him calling Justin Beiber “Johnny.”).

Larry makes up story about Sandy Koufax: In a 1991 Washington Post magazine profile, King is quoted as telling an audience in a Philadelphia synagogue one of his signature stories about the time he and the legendary pitcher drove to Connecticut from Brooklyn as teens to get ice cream. Koufax later told the reporter he and King weren’t friends and didn’t meet in Brooklyn, though they grew up in the same neighborhood. King couldn’t explain why he told that story for 30 years.

Larry confuses Ringo Starr with his dead bandmate George Harrison (2007) – Cool as it was to have the two living members of rock’s greatest band together in the Las Vegas interview, the mood has to curdle when you call one of them by the name of a dead colleague. Paul McCartney seemed to take it worse, pointing out the gaffe several times. A year later, Starr would get irritated when King said his age, then 68, many times in a solo interview (fun fact: Ringo’s only seven years younger than Larry!)  

Times researcher Carolyn Edds contributed to this report.