Lenny Wosniak (Steve Buscemi) is a private investigator occasionally hired by Jack. During his investigations, Wosniak will occasionally don a disguise as he sees fit. He claims he was once "part of a special task force of very young-looking cops who infiltrated high schools", in a reference to 21 Jump Street. While attempting to infiltrate the pages union by seducing Kenneth, Wosniak affixes a blond wig to assume the persona of the "nympho-coed Charlene LaRue"- the attempt ultimately fails as Kenneth was "impervious" to Mrs. LaRue's charms.
Appearances[]
He first appears in the second-season episode "The Collection", where (while spying on Jack to determine if he has any skeletons in his closet which could prevent him from being named the new CEO of General Electric) he discovers Jack has a large collection of homemade ceramic cookie jars.
Jack also hires him in the third season to obtain personal information about a man his mother was seeing, and (later) the true identity of his father. He finds out that the man his mother was seeing was married and narrows his father's identity to three men, leading Liz to put on a Mamma Mia style show to find Jack's father.
In "The Tuxedo Begins", Jack hires him after he is mugged.
In "Game Over" Lenny goes undercover at Kaylie Hooper's high school as a female drama teacher, Jan Foster, discovers that he prefers being Jan to being Lenny, and gets engaged to a female math teacher.