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| Episode 1 - [The Pilot (Love And Marriage)] |
| Details : When Grace receives an unexpected marriage proposal from her boyfriend Will tries to be supportive of her decision but finally tells her that she's making a mistake even though he's putting their friendship at risk. The situation is complicated by interference from Grace's socialite assistant Karen and Will's outrageous friend Jack. |
| Guest Cast and Crew : Leigh-Allyn Baker as Ellen | Gary Grubbs as Harlin Polk | Tom Gallop as Rob | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Sep. 21, 1998 | Rating ➦ ★★★★★★★★★★ |
| Episode 2 - [A New Lease On Life] |
| Details : Will must decide whether to support Grace's independence by encouraging her to take an apartment across town or selfishly keep her close by inviting her to share his living space. The decision may be made easier however by the nagging presence of Will's current roommate Jack and his parrot Guapo. Meanwhile Karen and Jack meet for the first time and find each other to be fabulous. |
| Guest Cast and Crew : Gary Grubbs as Harlin Polk | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Sep. 28, 1998 | Rating ➦ ★★★★★★★★★★ |
| Episode 3 - [Head Case] |
| Details : When Grace moves in with Will she complains that the guest bathroom is too small and suggests knocking the common wall down to create one big master bathroom which results in Will having to confront his own issues on change and his ability to have a successful relationship. Meanwhile Jack and Karen bear the brunt of Will and Grace's displaced anger. |
| Guest Cast and Crew : Gary Grubbs | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Oct. 05, 1998 | Rating ➦ ★★★★★★★★★★ |
| Episode 4 - [Between A Rock And Harlin's Place] |
| Details : When Grace decorates Harlin's apartment she gets carried away with a cowboy theme. Will is both shocked and embarrassed by the cowboy chic and makes an even greater mess of the situation. Meanwhile Jack decides to embark on a “singing career“ with a little help from Karen. |
| Guest Cast and Crew : Gary Grubbs as Harlin Polk | Tim Herzog as Bartender | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Oct. 12, 1998 |
| Episode 5 - [Boo! Humbug] |
| Details : Will and Grace plan to spend a serious Halloween together watching Ingmar Bergman movies at home--until Harlin drops off his over-eager kids at their place when he's called away on business. Meanwhile Jack convinces Karen to accompany him to the downtown parade where she becomes an honorary drag queen. |
| Guest Cast and Crew : Reiley McClendon as Nixon | Paul Goebel as Jerry | Gary Grubbs as Harlin Polk | Ben Caswell as Sam | Michael Stadvec as Starsky | Jorden Ashley as Buzzy Wuzzy | Demitri Corben as Drag Queen #1 | Terrence Michael as Drag Queen #2 | John Cantwell as Drag Queen #3 | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Oct. 26, 1998 | Rating ➦ ★★★★★★★★★★ |
| Episode 6 - [William Tell] |
| Details : When Jack reveals to Grace that Will once had an affair with a client she becomes paranoid that Will is keeping secrets from her. Her suspicions continue to grow when Will meets Karen for a discreet meeting to discuss her legal problems and will only tell Grace he's meeting with a client. |
| Guest Cast and Crew : Gary Grubbs as Harlin Polk | Phil Levesque as Delivery Man | Director : James Burrows | |
| Air Date : Nov. 09, 1998 |
| Episode 7 - [Where There's A Will There's No Way] |
| Details : Grace blames her relationship with Will as the reason for her lack of interest in dating and decides they can no longer have fun together. Meanwhile Jack enlists Will's help when the IRS catches up with him. |
| Guest Cast and Crew : Julian McMahon as Guy | Steve Paymer as Steve | Eric Gustavson as Sebastian | Todd Eckert as Jurgen Franzblau | Roy Fegan as IRS Auditor | Writer : Jhoni Marchinko | Director : James Burrows | |
| Air Date : Nov. 16, 1998 |
| Episode 8 - [The Buying Game] |
| Details : Grace has the opportunity to buy the studio that serves as her office space and turns to Will for first-time buyer advice. However Will's negotiating tactics lead Grace to believe that Will thinks she is incapable of closing the deal and she sets out to prove him wrong. Meanwhile Jack wants to become a massage therapist and practices his technique on a delighted Karen. |
| Guest Cast and Crew : Ivar Brogger as Mr. Hutt | Gary Grubbs as Harlin Polk | Writer : Dava Savel | Director : James Burrows | |
| Air Date : Nov. 30, 1998 |
| Episode 9 - [The Truth About Will And Dogs] |
| Details : After Grace defies Will's wishes and brings home a puppy Will can't resist the pooch and begins to treat him like a newborn baby. Meanwhile Jack and Karen worry about the dog's effect on Will and Grace and insist that the new parents go out for a night on the town. |
| Guest Cast and Crew : Anthony Meindl as Cute Guy | Leigh-Allyn Baker as Ellen | Gary Grubbs as Harlin Polk | Tom Gallop as Rob | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Dec. 15, 1998 |
| Episode 10 - [The Big Vent] |
| Details : Will and Grace become hooked on a real-life soap opera unfolding in their neighbors' apartment when they begin eavesdropping through the new heating vent in their floor. As Will and Grace live vicariously through the marital infidelities of the downstairs couple Jack feels neglected and enlists Karen's help in staging a play that drives the message home to his two best friends. |
| Guest Cast and Crew : Corinne Bohrer as Judy | Robert Curtis Brown as Will Actor | Jensen Daggett as Grace Actor | Writer : Jhoni Marchinko | Director : James Burrows | |
| Air Date : Jan. 05, 1999 |
| Episode 11 - [Will On Ice] |
| Details : It's Will's birthday and all he wants is a nice quiet dinner with his two best friends Grace and Jack. When Jack and Grace discover they share a passion for figure skating they surprise Will with tickets for Champions on Ice and Karen reluctantly joins the special evening. |
| Guest Cast and Crew : Rudy Galindo as Himself | Writer : Michael Patrick King | Director : James Burrows | |
| Air Date : Jan. 12, 1999 |
| Episode 12 - [My Fair Maid-Y] |
| Details : Will hires a cleaning lady to rescue his designing roommate Grace from the creative chaos that litters their apartment and while preparing for an annual decorators' contest Grace develops a dependency on her maid and can't create without her. Meanwhile Jack poses as an attorney in Will's office to impress an attractive guy he hopes to date. |
| Guest Cast and Crew : Wendie Jo Sperber as April | Raphael Sbarge as Alex | Writer : Adam Barr | Director : James Burrows | |
| Air Date : Feb. 02, 1999 |
| Episode 13 - [The Unsinkable Mommy Adler] |
| Details : Grace's visiting mom Bobbi Adler a would-be star whose propensity for breaking out into show tunes and impressions dismays her daughter – and delights Will Jack and Karen – wreaks havoc by suggesting Will and Grace wed despite their sexual differences. When Will winces at the fantasy of committing to anyone who needs to be the star of a relationship Grace realizes she's more of a chip off the old block than she imagined. |
| Guest Cast and Crew : Debbie Reynolds as Bobbi Adler | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : Feb. 09, 1999 |
| Episode 14 - [Big Brother Is Coming Part I] |
| Details : A surprise birthday party for Jack astounds Will when his estranged older brother Sam turns up at the fete at Grace's invitation. Not only do sparks fly between the brothers but electricity of a different sort crackles between Grace and Sam. Meanwhile Karen flashes her platinum card for Jack as the pair shop until they drop at a boutique where the snooty salesmen previously had snubbed Jack. |
| Guest Cast and Crew : John Slattery as Sam Truman | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Feb. 16, 1999 |
| Episode 15 - [Big Brother Is Coming Part II] |
| Details : A wary Grace tells Will of her romance with his brother Sam and unleashes an avalanche of resentment. While Will wrestles with sibling rivalry Karen helps Jack come to grips with turning 30 by hiring him as her personal assistant and leads Grace to sort through her true feelings for the Trumans. |
| Guest Cast and Crew : John Slattery as Sam Truman | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Feb. 23, 1999 |
| Episode 16 - [Yours Mine Or Ours] |
| Details : Stunned to find they have a 'date' with the same guy Will and Grace compete for the affections of a handsome charming new neighbor at dinner and even Jack's finely-tuned gaydar can't pick up his preference. Meanwhile Karen contemplates firing her driver and in a twist of irony asks Grace to role-play firing an incompetent employee. |
| Guest Cast and Crew : David Newsom as Peter | Writer : Rob Lotterstein | Director : James Burrows | |
| Air Date : Mar. 02, 1999 |
| Episode 17 - [Secrets And Lays] |
| Details : The gang retreats to a cabin in Vermont for the weekend where Grace rekindles romance with an old flame and tries to hide the fling from Will who's pining on the eve of his would-be anniversary. Meanwhile Karen's culinary efforts go up in smoke as does Jack's attempt to cheer Will by dragging him to a gay pub where the town barber-turned-hair stylist sidles up to him. |
| Guest Cast and Crew : David Sutcliffe as Campbell | Paul Gutrecht as Bartender Paul | Writer : Dava Savel | Director : James Burrows | |
| Air Date : Mar. 23, 1999 |
| Episode 18 - [Grace Replaced] |
| Details : Will finds a substitute Grace in Val a new neighbor who is available for plans with Will while Grace is consumed with work. As Will and Val continue to spend more time together Grace fears that she has been replaced and fights with Val to regain Will's attention. Meanwhile Jack seeks support from Karen after the court finds him guilty of slapping a meter maid and sentences him to pick up trash. |
| Guest Cast and Crew : Leigh-Allyn Baker as Ellen | Molly Shannon as Val Bassett | Tom Gallop as Rob | Director : James Burrows | |
| Air Date : Apr. 08, 1999 |
| Episode 19 - [Will Works Out] |
| Details : Will invites Jack to his gym on a buddy pass but when he expresses his embarrassment to Grace over his buddy's gay behavior Jack overhears the comments and looks to set him straight about prejudice. Meanwhile Grace continues to lend her ear when Karen's marriage hits rocky ground and she and Karen share an evening of girl talk. |
| Guest Cast and Crew : Ben Reed as Richard Keller | Writer : Michael Patrick King | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Apr. 22, 1999 |
| Episode 20 - [Saving Grace] |
| Details : A successful and arrogant New York publicist hires Grace to decorate his house with the condition that she fixes him up with Will. But there's a problem: Will can't stand the guy. Meanwhile Jack uses Karen to teach Will how to kiss someone he finds unattractive. |
| Guest Cast and Crew : Miguel Ferrer as Nathan Berry | Tiffany Fraser | Writer : Jhoni Marchinko | Director : James Burrows | |
| Air Date : Apr. 29, 1999 |
| Episode 21 - [Alley Cats] |
| Details : When Rob and Ellen admit that they don't have fun playing games with Will and Grace because of Grace's competitive nature Grace works to change her image. However as Grace loses her competitive edge Will's emerges and he convinces his partner to care only about winning. Meanwhile after learning how to administer CPR from Jack Karen saves a workman's life. |
| Guest Cast and Crew : Leigh-Allyn Baker as Ellen | John Capodice as Bernie the Workman | Lucky Vanous | Tom Gallop as Rob | Writer : Jhoni Marchinko | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : May. 06, 1999 |
| Episode 22 - [Object Of My Rejection] |
| Details : Will is stunned to discover that Grace is dating her ex-fiance Danny once again but he chooses not to interfere after he's accused of being meddlesome. Meanwhile Jack agrees to take a walk down the aisle with Karen's combative maid Rosario who needs a groom to help her smooth out some immigration problems. |
| Guest Cast and Crew : Franklin Cover as Justice of the Peace | Bob Morrisey as Man | Shelley Morrison as Rosario Salazar | Tom Verica as Danny | Writer : Adam Barr | Director : James Burrows | |
| Air Date : May. 13, 1999 |