He is also very insecure about his appearance: he is always concerned about the size of his "ass", which he thinks is too big, and he was unable to disguise his displeasure at Dana Carvey's impression of him in the show's fourth season.
He dates many women, such as Mimi Rogers, Sharon Stone, Ellen DeGeneres, and Dana Delany, but these relationships never last and are often doomed by elements of Larry's celebrity or work life.
The end of the series provided some hope for Larry; his decision to leave his show seemed to bring him a bit of perspective, and his relationship with Illeana Douglas appeared to be more substantial than his previous attempts at intimacy.
Hank Kingsley (all seasons) (born Henry Joseph Lepstein Jr.), played by Jeffrey Tambor, is the announcer and sidekick on The Larry Sanders Show, known for his "Hey now!"
Hank will often act humble and unassuming, especially on camera or in front of media executives and other influential persons, but would become condescending and often quite nasty to anyone whom he perceives to be of a lower status.
Following an alcohol-fuelled bachelor party at a strip club with Ed McMahon among the partiers, Hank and Margaret get married on the show with Alex Trebek officiating the ceremony.
The couple got divorced only a year later with Margaret initiating the split unable to deal with Hank's excessive personal and professional focus on Larry to the exclusion of everyone else in his life.
Artie is often shown drinking (typically either following a show taping or during a stressful situation), with his beverages of choice including vodka Salty Dogs and Glenlivet scotch whisky.
In season 6, Brian threatens to sue the show for sexual harassment after getting tired of Phil's gay jokes, but the suit is apparently called off after a surprising turn of events.
In the final episode ("Flip," original airdate 5/31/98), Brian tells Mary Lou that Hank offered him a job paying $300 a week ($503.50 in 2021 dollars) with no benefits, and he was thinking of taking it.
Based on working with and around him, the show staffers observed Phil's material to improve whenever he is emotionally unfulfilled as seen when his girlfriend dumps him and Larry describes the monologue as never having been that good before.
Phil frequently makes sexist and homophobic comments, and generally does not seem to like racial diversity on the show - mentioning that his Asian characters are often female because it is "killing two birds with one stone."
In the episode "The Matchmaker", she gets an inexperienced assistant, Mary Lou Collins, who makes frequent mistakes in research notes for Larry's interviews leading to several on-air embarrassing situations during the Nicollette Sheridan segment.
However, the arrangement quickly turns sour as Artie, already feeling disrespected and threatened by the whole proceeding, walks off the show following a disagreement with Paula over a production issue of lighting during which Larry takes her side.
Faced with a sudden crisis, Larry lets her produce that day's show by herself, before summoning her to his office to inform her that the arrangement won't work and ask her to see if the daytime job is still open.
As she's packing her stuff the next day, Artie approaches Paula at her desk and after imparting some words of wisdom from his long experience being a producer says that there are still some tricks that he could teach her, meaning that he had a change of heart and is now fine with her working alongside him.
Although generally pleased with Leo's representation, Larry is sensing that, when it comes to the latest contract negotiations, his agent might not be up to the task of going after "Letterman money"—something that the late-night host feels he deserves having done the show for six years.
His appearances on the show generally take place amid great turmoil and tension, such as contract negotiations, network sale, walk-off threats, and hosting takeover attempts.
Stevie says he's only there to "hold Levinson's hand" because he had signed him the previous week, but doesn't miss an opportunity to inquire about the contract renegotiation while encouraging Larry to keep on by telling him he's "got the network by the balls".
Talking things over with Artie at the office again, Larry calls his new agent "a prick", "a liar", "two-faced", and "weird" just as Stevie is coming into the room with a new offer from the network written on a piece of paper.
After meeting Richard "Dick" Jermaine who represents the foreign beer producer that's about to buy the network, Larry is so displeased with the overall vibe he gets from the man—particularly with his idea to overhaul the show into a "late night news magazine wrap-up of the day's events with a hip MTV sensibility"—that he immediately contacts Stevie about his options to leave, citing his inability to work for "this fucking beer nut" as the reason.
Faced with a difficult decision under severe pressure from his girlfriend Francine as well as the show's staff who are scared for their jobs, Larry is soon informed by Stevie that the ABC deal is almost locked up and is shown a one-year contract figure.
Unhappy with the lack of a long-term commitment on ABC's part, Larry wonders out loud to Stevie "if Harbert is such a big fan, how come the deal is only for a year".
Norman makes his first appearance in the episode "A Brush with the Elbow of Greatness" in order to handle the fallout following an incident involving Larry that occurred at a supermarket in Larchmont Village.
Local newscast runs a piece in which shopper named Carol Biederman accuses Larry of knocking her into a magazine rack by pushing in front of her in the checkout line.
Naturally, due to Larry's celebrity, the story generates some media interest that quickly goes into overdrive once the supermarket's security camera footage suddenly surfaces.
Depressed from the relentless beating he's taking in the media for what he did, Larry spends most of his time locked in his office saying he wants to quit show business and move to Montana.
Kenny Mitchell (seasons 2 and 6) is a network executive in his thirties played by Joshua Malina who is brought in to administer major changes to the Larry Sanders Show in order to make it appeal to a younger demographic.
Kenny is first introduced tagging along with Roger Bingham, when they drop into Larry's office unannounced in order to talk to him about "doing a little fine-tuning to get the numbers up" since he's losing to Keenan in certain key cities.
Roger Bingham (seasons 5–6) is a slick network executive in his mid-to-late thirties, played by Bruce Greenwood, who favours Jon Stewart to be the host over Larry.