The first season introduces Larry's post-Seinfeld world, where he is wealthy, has a loving wife and a best friend, and manages to offend many people around him.
Larry pitches the idea to various networks, but eventually alienates or offends everyone he makes a deal with, and anyone else attached to the project.
Larry works with Mel Brooks, Ben Stiller, Cady Huffman and David Schwimmer to star on Broadway in The Producers.
While at the courthouse for Marty's trial to speak on his behalf, Larry is confronted by Monena, who demands the money that he owes her.
Larry discovers that the judge is the same one who presided over his attempt to avoid jury duty, and has Monena pose as his girlfriend in order to clear Marty's name.
Larry thinks that he may have been adopted, because of a potentially misunderstood word his father said (and subsequently denies) while in the hospital, and hires a private investigator (Mekhi Phifer) to look into it.
When Larry runs into Cheryl for the first time since last season, he learns that she appreciated him more when he had a job, so he accepts NBC's offer for a Seinfeld reunion show to give her a part in it and win her back.
Guest stars include: Jerry Seinfeld, Julia Louis-Dreyfus, Jason Alexander, Michael Richards, Christian Slater, Richard Kind, Philip Baker Hall, Rosie O'Donnell, Catherine O'Hara, Elisabeth Shue, Meg Ryan, David Spade, Jillian Bell, Randall Park, and Eric Andre.
In order to avoid a charity gig, he goes with Jeff and Susie on a three-month trip to New York City, where he soon reunites with Leon.
He reveals to his therapist Dr. Thurgood (Fred Melamed) the traumatic experience: when Larry was a boy, he was playing strip poker with a girl in her father's Mister Softee truck; when the father finds them, he ejects a naked Larry from the truck, causing people on the street to laugh at him.
As a result of his error, Larry's softball team captain and mechanic Yari (Robert Smigel) refuses to fix his car, causing the passenger seat to become unstable.
For Jeff's birthday, Susie asks Larry to get a Mookie Wilson-autographed baseball at a card signing show.
Larry is accused of sexual harassment by his assistant Alice and his attempts to control the situation only serve to make things worse.
Leon breaks up with his girlfriend Mary Ferguson after purchasing non-refundable plane tickets to Asia for the pair.