When you ask me who I think the best talk show host on television is, my answer is always David Letterman. The Late Show with David Letterman on CBS was the first late night talk show I ever started watching regularly every night because I loved everything about the host. He wasn’t annoying like most television personalities who often try too hard to be funny and entertaining every single minute. He gave off a very anti-show business attitude and he talked like an ordinary guy who just happened to have a show on national television, which made his appeal similar to that of Johnny Carson. But he was a master of conversation and comedic timing and his self-deprecation often made him easy to love, even when he seemed grouchy. Which was another thing I appreciated about him. He was more honest than most people on television, which made him a somewhat controversial figure but one who was well-loved by the college-age anti-establishment generation that slowly began shaping television (and mainstream pop culture in general) at the end of the 20th century. Saturday Night Live kicked that door down earlier but Letterman brought it to Johnny Carson’s domain.

Born in Indianapolis, Indiana in 1947, David Letterman was a seemingly ordinary stock boy who bagged groceries at the local supermarket before he attended Ball State University in Muncie, Indiana where the Sigma Chi frat member spent a lot of time in the Department of Radio and Television, as an announcer and newscaster at the college radio station. Although he was fired for not taking his job seriously enough when he made fun of the music he had to play on the air.

Letterman considered Cincinatti broadcaster Paul Dixon his biggest inspiration when he decided to pursue a broadcasting career. And after graduating from Ball State in 1969, Letterman used his broadcasting experience to land a job as a weatherman in Indianapolis, which is how he got his start on television. Letterman was also experimenting with his comedy by making witty remarks and doing silly things like reporting the weather for fictitious cities. Letterman’s first national television exposure was as an ABC Sports pit road reporter at the Indianapolis 500, where he even got to interview Mario Andretti.

Letterman’s friends thought he was hilarious and they encouraged him to move to Los Angeles and write comedy. In 1975, Letterman and his wife moved to L.A. and he started performing stand-up comedy at The Comedy Store (where Jimmie Walker aka J.J. from Good Times recognized his talent and hired Letterman to write jokes for him). Afterwards Letterman jumped around Hollywood in the late seventies appearing on game shows, talk shows, variety shows and sitcoms, and in 1978 he caught the eye of talent scouts for The Tonight Show and appeared on the show to do stand-up comedy, becoming a regular favorite of Johnny Carson who enjoyed Letterman’s dry and sarcastic humor.

After Letterman’s appearances on The Tonight Show, NBC gave him his own comedy show in 1980 called The David Letterman Show which aired in the mornings. It was a funny show which critics liked and it won two Emmy awards, but it got no ratings and it was cancelled the same year after a few months. NBC decided to give Letterman a shot in late night instead and this would end up being a smart move.

Late Night with David Letterman began airing on NBC in 1982, following Johnny Carson and replacing The Tomorrow Show with Tom Snyder. Former SNL band member Paul Shaffer was Letterman’s sidekick, band leader and musical director and Bill Murray was his first guest. The show was just as quirky and irreverent as Letterman himself. His antics were very popular with college-age viewers who liked the show’s unpredictable and edgy nature, which helped the show develop a cult following. The show became known for Letterman’s documentary-like man-on-the-street segments (something many talk shows do today but was new at the time), segments like “Stupid Pet Tricks” and the “Top Ten List” and such antics as dropping watermelons off five-story buildings and attaching cameras to dogs.

David Letterman often played it straight while letting the madness unfold around him, like a modern-day Jack Benny. But Letterman was the first comedian to bring a certain brand of youthful anarchy to late night talk shows that paved the way for talk show hosts like Conan O’Brien, Jimmy Kimmel and Jimmy Fallon. And he would often involve his crew in the comedy bits. Not just Paul Shaffer but announcer Bill Wendell, stage manager Biff Henderson and producers, directors, stage hands and writers.

Speaking of writers, this show had some of the best in show business. Among the talented writing staff was Merrill Markoe who was heavily involved in establishing the show’s style as she created the segments “Stupid Pet Tricks,” “Stupid Human Tricks,” “Viewer Mail” and many of the remote segments; Chris Elliott who would play many oddball characters in the show’s comedy skits which would lead to him becoming a character actor in other shows like Everybody Loves Raymond, Eagleheart and Schitt’s Creek; long-time head writer Steve O’Donnell who would go on to write for The Late Show with David Letterman, The Bonnie Hunt Show, The Chris Rock Show, The Man Show and Jimmy Kimmel Live! in addition to episodes of Seinfeld, The Simpsons and Space Ghost Coast to Coast; Rob Burnett, co-creator of the TV comedies Bonnie, Ed and The Knights of Prosperity who would also executive produce The Late Show with David Letterman; Randy Cohen, later a writer and co-executive producer on Michael Moore’s news satire TV Nation and head writer on The Rosie O’Donnell Show; Kevin Curran, producer of Married…with Children and The Simpsons; Fred Graver, later a writer for In Living Color and The Jon Stewart Show; Larry Jacobson, who would later produce Married…with Children, write for Letterman on The Late Show and write for Jay Leno on The Tonight Show; Joe Toplyn, later a writer on In Living Color, The Tonight Show with Jay Leno and The Late Show with David Letterman and a writer and producer on Monk; Matt Wickline, later a writer on In Living Color who would go on to co-create The Hughleys and Cedric the Entertainer Presents.

Letterman also became known for his memorable interviews which sometimes took a bad turn due to his unfriendly persona which sometimes clashed with the personalities of celebrities, some of whom admitted they were afraid of going on the wild show. Some of the best interviews included those with Charles Grodin, Andy Kauffman, Teri Garr, Jack Hanna, Howard Stern, Marv Albert, Harvey Pekar and Cher (who called Letterman an asshole on the air).

After Johnny Carson retired in 1992, many TV insiders speculated that Letterman might take over The Tonight Show, but NBC gave the job to popular Tonight Show guest host Jay Leno instead, which led to Letterman’s departure from NBC to CBS where he hosted The Late Show with David Letterman from 1993 to 2015 at the same famous New York theater where they filmed The Ed Sullivan Show.

The Late Show, much to the surprise of TV critics and David Letterman’s own fans, was not as irreverent as Late Night. Letterman seemed to be a little more classy and his talk show was more traditional, with a longer monologue, more serious interviews and even a name change for Paul Shaffer’s band which used to be called the World’s Most Dangerous Band but was now called the CBS Orchestra with the addition of a brass section.

The show was still witty and irreverent, but it was more sophisticated and had broader appeal than Late Night, garnering acclaim from critics and TV viewers alike with Letterman a regularly popular and well-respected host, comedian and TV personality for the show’s entire run. And many celebrities eventually grew to love him too.

Following Letterman’s departure from The Late Show in 2015, Letterman explored new avenues joining the global warming-themed NatGeo docuseries Years of Living Dangerously as a celebrity correspondent travelling to India to investigate their energy conservation efforts and co-hosting the Turner Classic Movies series The Essentials with Alec Baldwin in 2017, but he returned to the talk show scene in 2018 with the hour-long Netflix show My Next Guest Needs No Introduction with David Letterman. Each episode featured a long and in-depth one-on-one interview with a single celebrity and it got a positive reception for its insightful conversations. The first season featured interviews with Barack Obama, George Clooney, Malala Yousafzai, Jay-Z, Tina Fey and Howard Stern, the second season featured Kanye West, Ellen DeGeneres, Tiffany Haddish, Lewis Hamilton, Melinda Gates and Shah Rukh Khan and the third season featured Kim Kardashian, Robert Downey Jr., Dave Chappelle and Lizzo.

Everyone calls Johnny Carson the king of late night but in my mind, Letterman is really the best. He was razor sharp and more adept at spinning every moment into comedy gold with his creative and often bizarre sense of humor. I was sad when his Late Show run ended and Letterman retired from weekly late night comedy because I knew there was literally no one else like him on television and most likely there would never be anyone else like him again. I liked a few of Letterman’s late night predecessors, including Carson, but Letterman was the first one to inspire devotion from me because he broke all the rules of late night comedy by making fun of late night comedy and all the phony things about show business while simultaneously evolving and adapting it, which often made his talk shows feel like some of the most smart and creative stuff on TV.