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| Episode 1 - [The Third Wheel Gets The Grace] |
| Details : Will returns from vacation to discover that Grace's romantic relationship with neighbor Nathan is humming along. Nathan feels neglected when Will and Grace resume their chummy friendship complete with their own private language and code. Meanwhile Jack proudly takes his new-found son Elliot shopping for school at Barney's while Rosario and Karen each cruise the merchandise looking for the perfect anniversary gift. |
| Guest Cast and Crew : Michael Angarano | Woody Harrelson | Jacqueline Beatty | Karin Co | Jessica Dean | Debra K. Beatty as Woman #4 | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Sep. 27, 2001 |
| Episode 2 - [Past And Presents] |
| Details : The new lawyer in Will's firm is the same lout who bullied him as a child; Nathan's birthday flusters Grace who's outdone in the gift department by Karen. |
| Guest Cast and Crew : Adam Goldberg | Woody Harrelson | Walter Addison | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Oct. 04, 2001 |
| Episode 3 - [Crouching Father Hidden Husband] |
| Details : Jack is puffed up with paternal pride as he escorts his long-lost teenaged son Elliot to a junior high school dance but not before he coerces Grace into posing as Elliot's date – which only revives her own tortured memories of rejection from school dances many years before. Elsewhere Karen has great fun at her lawyer Will's expense when she continues to capriciously summon him for bogus emergencies – that is until she really needs him. |
| Guest Cast and Crew : Victor Brandt | Kari Lizer | Michael Angarano | Landry Allbright | Sydney Berry | Hep Jamieson | Writer : Adam Barr | Director : James Burrows | |
| Air Date : Oct. 11, 2001 |
| Episode 4 - [Prison Blues] |
| Details : After Stan is arrested for tax evasion Grace and Karen timidly visit him in prison. Grace is so moved to help her worried friend that she moves right into Karen's deluxe apartment-in-the-sky where she becomes a demanding guest who's soon hooked on servants bubble baths and an extravagant lifestyle. Meanwhile as Stan's attorney Will struggles with stage-fright when he babbles on during a TV news interview so Jack convinces him to polish his communication skills by attending an acting class ruled by an imperious teacher. |
| Guest Cast and Crew : Brent Sexton | Eileen Brennan | James Black | Margaret Scarborough | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : Oct. 18, 2001 |
| Episode 5 - [Loose Lips Sink Relationships] |
| Details : In a sneaky ploy to bum a night off from work at Barney's department store a conniving Jack plays matchmaker and takes advantage of his geeky female supervisor's interest in Will while mindful of Will's fantasy of modeling in the store's catalogue. Jack parlays their mutual desires into a date even though his unsuspecting friend doesn't have a clue of her intentions. Elsewhere Grace goes where no woman should when she compares her previous sexual experience with her boyfriend Nathan's. |
| Guest Cast and Crew : Parker Posey | Woody Harrelson | Andrew Rosenbach | Director : James Burrows | Writer : Kari Lizer | |
| Air Date : Oct. 25, 2001 |
| Episode 6 - [Rules Of Engagement] |
| Details : During an intimate moment Nathan pops the question of marriage to Grace but she recoils simply because the situation didn't fit her childhood fantasy of a proposal. When she realizes her mistake she returns the favor but doesn't get the response she hoped she'd get. |
| Guest Cast and Crew : Dean Cameron | Woody Harrelson | Sam Pancake | Jordan Feldman | Shane Partlow | Director : James Burrows | Writer : Jeff Greenstein | |
| Air Date : Nov. 01, 2001 |
| Episode 7 - [Bed Bath And Beyond] |
| Details : While a baleful Grace wallows in bed as she grieves over losing her boyfriend Nathan an enterprising Will tries all his old tricks to spring her from her mattress and back into the real world's whirl. But when Jack and Karen arrive Will fears that their bizarre efforts to help might actually drive Grace futher into her shell -- not to mention therapy. |
| Guest Cast and Crew : Writer : Jhoni Marchinko | Director : James Burrows | |
| Air Date : Nov. 08, 2001 |
| Episode 8 - [Star-Spangled Banter] |
| Details : Will and Grace elect to disagree when it comes to choosing sides during a mayoral election; she supports the female Jewish candidate and he's voting for the gay nominee. To settle matters the roomies host fund-raisers attended simultaneously by both aspirants. |
| Guest Cast and Crew : Anne Meara | Michael Angarano | Marshall Manesh | Douglas Sills | Cynthia Mann | Michael Taylor Gray | Director : James Burrows | |
| Air Date : Nov. 15, 2001 |
| Episode 9 - [Moveable Feast Part 1] |
| Details : Rather than be apart on Thanksgiving Day Will and Grace join Jack and Karen for a festive holiday motor tour of their respective dysfunctional families including Grace's domineering mother as well as Will's willful mom and Jack's stepdad -- with unsettling results. Meanwhile back home a waiting Rosario bastes and tastes their juicy turkey. |
| Guest Cast and Crew : Jon Tenney | Helen Slater | Kenneth Mars | Blythe Danner | Neil Vipond | Debbie Reynolds as Bobbi Adler | Nick Offerman | Beau Bridges | Lainie Kazan | Director : James Burrows | Writer : Kari Lizer | |
| Air Date : Nov. 22, 2001 |
| Episode 10 - [Moveable Feast Part 2] |
| Details : This episode is also known as Thanksgiving. Will and Grace join Jack and Karen in a motor tour of their respective families. (Double-length Episode) |
| Guest Cast and Crew : Jon Tenney | Helen Slater | Michael Angarano | Kenneth Mars | Blythe Danner | Neil Vipond | Debbie Reynolds as Bobbi Adler | Nick Offerman | Beau Bridges | Lainie Kazan | Director : James Burrows | Writer : Kari Lizer | |
| Air Date : Nov. 22, 2001 |
| Episode 11 - [Stakin' Care Of Business] |
| Details : At the gym Will spies another guy who looks maddeningly familiar while Jack gets a workout as he keeps repeating one of his nonsensical catchphrases in hopes of seeing it become popular among the sweat set. Meanwhile Grace gets some bad advice from Karen when she seeks a loan to expand her company so she stoops to asking her wealthy employee herself for the money—even if she has to resort to drastic measures to get the point across. |
| Guest Cast and Crew : Patrick Breen | Dan Gauthier | Director : James Burrows | Writer : Bill Wrubel | |
| Air Date : Dec. 06, 2001 |
| Episode 12 - [Jingle Balls] |
| Details : Grace is hired as seasonal help to decorate the Christmas display windows of fashionable Barney's; Will meets a ballet dancer but is too embarrassed to introduce his friends. |
| Guest Cast and Crew : Parker Posey | Larry Sullivan | Paul Keith | Writer : Laura Kightlinger | Director : James Burrows | |
| Air Date : Dec. 13, 2001 |
| Episode 13 - [Whoa Nelly] |
| Details : Will And Grace try to lure Tina Will's dad's mistress away from Will's father by setting her up with another man. Unfortunately the only man available is Will's gay friend Larry. Also Karen buys a horse for breeding but the stud is more interested in stallions. |
| Guest Cast and Crew : Tim Bagley | Lesley Ann Warren | Morgan Nagler | Cal Bartlett | Writer : Adam Barr | Director : James Burrows | |
| Air Date : Jan. 10, 2002 |
| Episode 14 - [Grace In The Hole] |
| Details : While visiting Karen's incarcerated husband Grace re-discovers a handsome high school friend who's also doing time in prison and despite Will's advice she's soon dressing up and visiting the inmate while dreaming of a life together outside the Big House. Conversely a sympathetic Rosario chides Karen for not standing by her man – and bets her boozy boss that she and pal Jack cannot stay penned-up together in the same room for three days without harming each other. |
| Guest Cast and Crew : Brent Sexton | Kirk Baltz | Cheryl Bricker | Steven Shaw | Director : James Burrows | Writer : Bill Wrubel | |
| Air Date : Jan. 17, 2002 |
| Episode 15 - [Dyeing Is Easy Comedy Is Hard] |
| Details : Rosie O'Donnell plays Bonnie a no-nonsense single mom who clashes with Jack over the raising of their son Elliot fathered from Jack's sperm-bank donation. Bonnie's enraged because Jack had 12-year-old Elliot's hair bleached blond so she lays down the law. From now on she tells him stay out of my kid's life. I don't want you to see him again. A parallel storyline unfolds at a wedding gala where Will poses as a tennis pro (because nobody likes lawyers); and Grace caustically toasts the bridegroom her ex-fiancé. I've always thought about having a child she says. But not as a husband. |
| Guest Cast and Crew : Jennifer Aspen | Jim Hanna | Michael Angarano | Tom Verica as Danny | Maggie Wheeler | Greg Vaughan | Rosie O'Donnell | Director : James Burrows | |
| Air Date : Jan. 31, 2002 |
| Episode 16 - [A Chorus Lie] |
| Details : Matt Damon makes a guest appearance as a clever charmer named Owen who's competing against Jack for a spot in New York's Gay Men's Chorus. Truth be told however Owen is totally straight and is really after the group's big perk: a summer trip to Europe all-expenses paid. Jack suspects Owen's ruse but needs proof. How about the hug test? Now a flustered Jack reluctantly turns to Grace to in Owen. Meanwhile a scheming Karen tries to pass off an unwitting Will as her lover and not her lawyer when she discovers that she's the object of pity for being single at her own Valentine's Day party |
| Guest Cast and Crew : Matt Damon | Patrick Kerr | Leslie Jordan | Amanda Carlin | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Feb. 07, 2002 |
| Episode 17 - [Someone Old Someplace New Part 1] |
| Details : Will and Grace feel they need more elbow room so they search for larger digs and find an exquisite place—despite the efforts of Sandra Bernhard—but to finance the move they illegally sub-let their old apartment. Meanwhile a well-intentioned Jack begins filming a documentary of Karen's colorful life to celebrate her birthday but accidentally stumbles upon her estranged lowlife mom. |
| Guest Cast and Crew : Sandra Bernhard | Leigh-Allyn Baker as Ellen | Suzanne Pleshette | Tom Gallop | Joseph Will | Jamison Jones | Writer : Jhoni Marchinko | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : Feb. 28, 2002 |
| Episode 18 - [Something Borrowed Someone's Due Part 2] |
| Details : After Will and Grace move into their expansive new dream apartment they discover the awful pangs of separation anxiety as they pine for their smaller old digs now happily occupied by their friends who sub-let the place. Elsewhere Jack tries to reconcile Karen with her estranged grifter of a mom who wants to recruit her daughter for her next caper. |
| Guest Cast and Crew : Leigh-Allyn Baker as Ellen | Suzanne Pleshette | Tom Gallop | Joseph Will | Mickey Maxwell | Writer : Adam Barr | Director : James Burrows | Writer : Bill Wrubel | |
| Air Date : Mar. 07, 2002 |
| Episode 19 - [Cheatin' Trouble Blues] |
| Details : Will presents his newly reconciled parents with a cruise for their anniversary but their individual secrets ruin his hopes. |
| Guest Cast and Crew : Sydney Pollack as George Truman | Blythe Danner | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : Mar. 28, 2002 |
| Episode 20 - [Went To A Garden Potty] |
| Details : In the aftermath of his parents' divorce Will salvages a beloved garden gnome – nicknamed Squatsie – and proudly plants the childhood relic in his apartment's community area until Grace accidentally delivers a coup de grace on the gnome's dome with a shovel. Elsewhere Jack consults his acting coach when he fears that his heterosexual role in a mattress commercial produced by Karen will stereotype him for more meaningful gay acting gigs in the future. |
| Guest Cast and Crew : Peter MacKenzie | Tom Poston | Eileen Brennan | Melissa Russell | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Apr. 04, 2002 |
| Episode 21 - [He Shoots They Snore] |
| Details : Teaching a design seminar challenges Grace; chaperoning Jack's son occupies Will at the youth's basketball tourney. |
| Guest Cast and Crew : Brian Howe | Michael Angarano | Landry Allbright | Paul Parducci | Irene White | Debra Azar | Ray Porter | Gabriel Bologna | Tony Pasqualini | Ali Chen | Director : James Burrows | |
| Air Date : Apr. 11, 2002 |
| Episode 22 - [Wedding Balls] |
| Details : Will expects two friends to arrive in New York to plan a wedding but when the bride-to-be falls ill he asks a willing Grace to work with the clueless groom to work out the details – but she gets a little too involved in the dreamy details and fancies herself a bride instead. Meanwhile Will and Karen get chummy over a steamy potboiler book that they're both reading which leaves a jealous Jack fuming as the odd man out in the book-of-the-month club. |
| Guest Cast and Crew : Tracy Nelson | Kimberly Scott | Steven Shenbaum | Stephanie Erb | Nicole Forester | Tia Riebling | Judy Nazemetz | Writer : Laura Kightlinger | Director : James Burrows | |
| Air Date : Apr. 18, 2002 |
| Episode 23 - [Fagel Attraction] |
| Details : After his laptop computer is stolen Will meets a sociable police detective who takes a special interest in his case as they go undercover – but Will doesn't know that the gumshoe is secretly participating in Jack's therapy group for gays. Elsewhere Grace is again hassled by her psycho neighbor Val who opens a rival design business and prospers by stealing Grace's ideas. |
| Guest Cast and Crew : Fred Applegate | Michael Douglas | Barry Livingston | Molly Shannon as Val Bassett | Kevin Fabian | Writer : Jenji Kohan | Director : James Burrows | |
| Air Date : Apr. 25, 2002 |
| Episode 24 - [Hocus Focus] |
| Details : After Will wins a portrait session at a charity auction he takes Grace to pose for a notoriously eccentric celebrity photographer but the unfocused shooter's bizarre methods ultimately produce a funky image that flatters Grace – and frightens Will. Meanwhile Jack's back with another performance act and this time he employs magic tricks but regrets using Karen as his assistant. |
| Guest Cast and Crew : Jason Stuart | J.P. Manoux | Glenn Close | Jeremy Forte | Director : James Burrows | |
| Air Date : May. 02, 2002 |
| Episode 25 - [A Buncha White Chicks Sittin' Around Talkin'] |
| Details : When Will hears his biological clock ticking he shocks Grace by asking her to become the mother of his baby but when they meet with a therapist Grace reveals that she's uneasy about the necessary sacrifices – and makes a startling revelation. Inspired by Will's seize-the-day quest Jack and Karen are also moved to pursue their goals: for him it's auditioning for a legitimate Broadway production; for her it's visiting her imprisoned husband for a dreaded conjugal visit. |
| Guest Cast and Crew : Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : May. 09, 2002 |
| Episode 26 - [Ai Artificial Insemination Part 1] |
| Details : After Will and Grace decide to have a baby together obstacles pile up before them including a missing specimen sample and bungled insemination efforts that have them teetering between artificial and natural means – all leading to mis-conceptions. Meanwhile when Jack considers giving up his show-business aspirations until he gets some career advice from a divine entity – his idol Cher. Likewise married Karen is sorely tempted by the romantic tickling of a rich and natty gentleman. |
| Guest Cast and Crew : Rip Torn | Laura Kightlinger as Nurse | Michael Angarano | Cher as Cher | Andrew Rosenbach | J. Lucas | Charles C. Stevenson Jr. | Richard Assad | Peggy Lane | Writer : Adam Barr | Director : James Burrows | |
| Air Date : May. 16, 2002 |
| Will And Grace Season 4 Episode 27 |
| Episode 27 - [Ai Artificial Insemination Part 2] |
| Details : After Will and Grace decide to have a baby together obstacles pile up before them including a missing specimen sample and bungled insemination efforts that have them teetering between artificial and natural means—all leading to mis-conceptions. Meanwhile Jack considers giving up his show-business aspirations until he gets some career advice from a divine entity: his idol Cher. Likewise married Karen is sorely tempted by the romantic tickling of a rich and natty gentleman. |
| Guest Cast and Crew : Rip Torn | Laura Kightlinger as Nurse | Cher as Cher | Writer : Alex Herschlag | Director : James Burrows | Writer : Jeff Greenstein | |
| Air Date : May. 16, 2002 |