<Li> Stuart Lamarack, played by Dave Foley, is a client of Will's who becomes Jack's longest relationship, until Jack cheats on him . </Li> <Li> Jack has countless short - term lovers over the course of the series (and presumably long before and after), although most are never mentioned by name, or mentioned at all; it is constantly assumed, and not always stated, that he has multiple boyfriends in every episode . Due to Jack's promiscuity, and his habit of forgetting his boyfriends' names, it would be literally impossible to list all of his love interests over the course of the show . Will jokes that if he was to avoid every man that Jack has ever slept with, "That would leave me with...women!", Grace jokes that if everyone stopped working for every man that broke his heart "The city would shut down". Jack also comments that he goes on thousands of dates a year . </Li> <Ul> <Li> Lorraine Finster, played by Minnie Driver, is Stan's mistress . She is a slutty prison cafeteria worker (and, it is implied, prostitute) who instantly forms a hatred of Karen . She was Karen's stepdaughter very briefly (for about 20 minutes) when Lyle, her father, marries Karen . Lorraine was unable to attend the wedding due to an aggressive strain of herpes that kept her from flying . According to the episode "The Accidental Tsuris" she was raised as a girl, despite being genetically male or perhaps a hermaphrodite . It is implied she was estranged from her father for several years and may have been born out of wedlock . </Li> <Li> Harlin Polk, played by Gary Grubbs, is a major client of Will's in season one who ultimately fires him . </Li> <Li> Mrs. Freeman, played by Jo Marie Payton, is an executive assistant at Doucette & Stein, her most commonly uttered phrase is "Mm - hmm" which is often said with sass . </Li> <Li> Zandra Zoggin, played by Eileen Brennan, is Jack's crusty acting coach and a chain - smoking former Hollywood star . After Jack takes over her class, Zandra loses her interest in life and ends up in an actor's retirement village . </Li> <Li> Dr. Jay Markus, played by Tom Skerritt, is Leo's father and Grace's eventual father - in - law . She meets him during brunch, thinking he is one of Leo's "old friends". </Li> <Li> Eleanor Markus, played by Judith Ivey, is Leo's mother and a noted author of three books on theatre; she meets Grace during brunch alongside her husband . She also is the first to tell her new daughter - in - law her son's actual name, Marvin . </Li> <Li> Mr. Stein, played by Gene Wilder, is the senior partner at Will's firm, an eccentric man who takes a liking to Will . He refers to Will as "Gay Will," but without at first realising that Will is actually gay . He and Karen are attracted to each other, but nothing comes of it . He is away from the office for some time prior to season 5 due to a mental breakdown and subsequent incarceration in a mental facility; having been referred to in the company letter - head as running "The London Office" in his absence . </Li> <Li> Margot, played by Lily Tomlin, is a senior partner at Will's firm, who apparently takes over after Mr. Stein . She is also quite eccentric and sarcastic . She promotes Will to partner . </Li> <Li> Dorleen, played by Parker Posey, is Jack's bitchy, chain - smoking boss during his brief tenure at Barneys New York . </Li> <Li> Mr. Zamir, played by Marshall Manesh, is an obnoxious tenant in Will and Grace's building, with a tendency to take off his shirt and to steal Will and Grace's newspapers . </Li> <Li> Benji, played by Brian A. Setzer, is Beverley Leslie's "business associate" and boytoy . </Li> <Li> Joanne, played by Emily Rutherfurd, is a student of Zandra's acting class who becomes a devoted follower of Jack and his "McFarland method". </Li> <Li> Russell, played by Jon Fleming, is a handsome, muscular student of Zandra's acting class who is often asked by Jack to take his shirt off when Jack is teaching the "McFarland method". </Li> <Li> Julius, played by Neil Vipond, is Bobbi Adler's close friend and a pianist . </Li> <Li> Gary, played by Jamie Kaler, is Will's coworker at Doucette and Stein . </Li> <Li> Nurse Sheila, played by Laura Kightlinger, is a rather creepy nurse who works at the sperm bank (where Will visits, intending to donate sperm to his high - school friend Claire). She openly admits she is a whore in season 4 (when Will and Grace are planning to have a baby together), and thereafter seems to appear whenever Will goes into a hospital . She is pregnant in season 8 and attends birth - classes alongside Grace . Her brother, a doctor played by guest - star Jack Black (Kightlinger's real - life former boyfriend), claims he would be "tappin' that big time" if they weren't related . </Li> <Li> Dave, played by Mathew Botuchis, is the only openly straight worker at OutTV, the gay network where Jack works in the last seasons . Jack is unimpressed with his heterosexuality and instead refers to him as Elizabeth . </Li> <Li> Jamie, played by John Ducey, is the station manager at OutTV . </Li> <Li> Tim, played by Mark Harelik, is a member of Senior Management at OutTV . </Li> <Li> Jimmy, played by Sam Pancake, is a colleague of Jack's at OutTV . </Li> <Li> Smitty, played by Charles C. Stevenson Jr, is a bartender who regularly serves Karen at different establishments . She has been known to call other bartenders "Smitty", even when they tell her it isn't their name . If Karen is depressed Smitty will tell her a tragic story about his own life, which she will laugh at thinking it is a joke . </Li> </Ul> <Li> Lorraine Finster, played by Minnie Driver, is Stan's mistress . She is a slutty prison cafeteria worker (and, it is implied, prostitute) who instantly forms a hatred of Karen . She was Karen's stepdaughter very briefly (for about 20 minutes) when Lyle, her father, marries Karen . Lorraine was unable to attend the wedding due to an aggressive strain of herpes that kept her from flying . According to the episode "The Accidental Tsuris" she was raised as a girl, despite being genetically male or perhaps a hermaphrodite . It is implied she was estranged from her father for several years and may have been born out of wedlock . </Li>

Who plays will's boss on will and grace