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| Episode 1 - [Guess Who's Not Coming To Dinner] |
| Details : Despite her moving out (to across the hall) Will still feels that Grace clings to him so she asserts her independence by having a dinner party without him. Meanwhile to keep the INS at bay Jack is forced to move in with Rosario. |
| Guest Cast and Crew : Leigh-Allyn Baker as Ellen | Shelley Morrison as Rosario Salazar | Tom Gallop as Rob | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Sep. 21, 1999 |
| Episode 2 - [Election] |
| Details : When Grace feels that Will is abusing his power as president of the tenant's association she runs against him. Karen tries to buy back Jack's forgiveness when she lets his beloved bird Guapo fly out the window. |
| Guest Cast and Crew : Shelley Morrison as Rosario Salazar | Shirley Prestia as Mrs. Pressman | Lou Cutell as Mr. Arthur Pressman | Marshall Manesh as Mr. Zamir | Lyn Alicia Henderson as Nurse | Writer : Adam Barr | Director : James Burrows | |
| Air Date : Sep. 28, 1999 |
| Episode 3 - [Das Boob] |
| Details : A deceiving but flattering newspaper photo makes Grace look more endowed than she really is and gains her the attention of a former high school heartthrob who was never one to keep abreast of her before. Jack is destroyed to learn that Will had a fling with Walter Jack's ex-boyfriend. |
| Guest Cast and Crew : Scott Patterson as John Gregorio | Anthony DeSantis as Walter | Writer : Jhoni Marchinko | Director : James Burrows | |
| Air Date : Nov. 02, 1999 |
| Episode 4 - [Whose Mom Is It Anyway] |
| Details : Grace is jealous when her mother stops match making for her and instead sets Will up. Jack must convince an INS agent (who he dated once) that he and Rosario are happily married. |
| Guest Cast and Crew : Peter Paige as Roger O'Neil | Shelley Morrison as Rosario Salazar | Debbie Reynolds as Bobbi Adler | Andy Comeau as Andy Fellner | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : Nov. 09, 1999 |
| Episode 5 - [Polk Defeats Truman] |
| Details : When his work for Harlin takes up all his time Will drops all his other legal clients; a decision that later comes up to bite. Meanwhile Grace tries to teach Karen how to live on a budget. |
| Guest Cast and Crew : Gary Grubbs | Elaine Bromka as Outlet Shopper | Director : James Burrows | Writer : Jeff Greenstein | |
| Air Date : Nov. 16, 1999 |
| Episode 6 - [To Serve And Disinfect] |
| Details : An unemployed Will agrees to serve as one of Jack's cater-waiters until he learns that he'll be catering for American Bar Association. Grace discovers Karen's darkest secret: she once made a porn video. |
| Guest Cast and Crew : Terry Kiser as Carl | Brian Palermo as Brian Kelly | Kim Robillard as Brent | Alex Boling as Stuart | Brian Jacobs as Michael the Cater Waite | Director : James Burrows | |
| Air Date : Nov. 23, 1999 |
| Episode 7 - [Homo For The Holidays] |
| Details : Will and Grace are shocked to learn that Jack never told his mother he was gay and encourage him to open up to her at Thanksgiving. The evening brings a revelation for Jack as well: his father isn't who he thinks it is. |
| Guest Cast and Crew : Veronica Cartwright as Judith McFarland | Writer : Alex Herschlag | Director : James Burrows | |
| Air Date : Nov. 25, 1999 |
| Episode 8 - [Terms Of Employment] |
| Details : Grace looks to Will for representation when a hotshot lawyer doesn't pay her for a consulting assignment but he ends up making Will a job offer. Meanwhile Jack and Karen turn a training film set into an adult entertainment experience. |
| Guest Cast and Crew : Jo Marie Payton as Mrs. Freeman | Gregory Hines as Ben Doucette | Aaron Lustig as Marv | Bob Clendenin as Bob Dent | Dan Sachoff as Announcer | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Nov. 30, 1999 |
| Episode 9 - [I Never Promised You An Olive Garden] |
| Details : Tired of Rob and Ellen's low-rent taste in dining Will and Grace start hanging with a pair of hip downtowners they meet at a sushi joint. But as the new pals paint the town Rob and Ellen see red when they catch their best friends lying to avoid plans to dine at their favorite eatery: a coupon-crazy Italian chain in Secaucus. Meanwhile Jack's inner child gets a little pick-me-up when he joins Karen at a PTA meeting at her kid's school. |
| Guest Cast and Crew : Penn Badgley as Todd | Leigh-Allyn Baker as Ellen | Steve Valentine as Kai | Tamlyn Tomita as Naomi | Tom Gallop as Rob | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Dec. 14, 1999 |
| Episode 10 - [Tea And A Total Lack Of Sympathy] |
| Details : When they appear on their favorite TV show Antiques on the Road Grace can't wait to dress down the guests who are ever hopeful that their tchotchkes are worth a fortune while Jack just wants to undress the show's attractive appraiser Porcelain Paul. But then it's all business when they realize that their junky thrift-store teapot is actually valued at $30000. Meanwhile Will's new boss makes the reluctant lawyer kiss up to Karen in hopes of landing her hubby as a client. |
| Guest Cast and Crew : Jo Marie Payton as Mrs. Freeman | Gregory Hines as Ben Doucette | David St. James as Smitty | Connie Sawyer as Old Woman | Lauren Tuerk as Woman | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Jan. 11, 2000 |
| Episode 11 - [Seeds Of Discontent] |
| Details : Grace is excited to meet Will's best friend from high school until she learns that the woman has made a request: to be implanted with Will's sperm. Now Grace has to confront Will about Will being her backup. |
| Guest Cast and Crew : Megyn Price as Claire | Laura Kightlinger as Nurse | Writer : Jhoni Marchinko | Director : James Burrows | |
| Air Date : Jan. 25, 2000 |
| Episode 12 - [He's Come Undone] |
| Details : Erotic dreams about Grace send Will to a therapist who seems more interested in Grace. Meanwhile Jack and Karen clash over her treatment of Rosario. |
| Guest Cast and Crew : Markus Flanagan as Dr. Loranger | Shelley Morrison as Rosario Salazar | Writer : Adam Barr | Director : James Burrows | |
| Air Date : Feb. 08, 2000 |
| Episode 13 - [Oh Dad Poor Dad He's Kept Me In The Closet And I'm So Sad] |
| Details : Will's ideal relationship with his loving father sours when his dad prepares to accept an award at his company's dinner banquet but tries to dissuade his son from attending because he's told everyone that Will is married to Grace. Meanwhile Karen's private detective finds Jack's biological father. |
| Guest Cast and Crew : Perry King as John Marshall | Sydney Pollack as George Truman | Mimi Cozzens | Joe Ochman as Chuck | Director : James Burrows | |
| Air Date : Feb. 15, 2000 |
| Episode 14 - [Acting Out] |
| Details : Will and Jack appear on Today to protest NBC for cutting a gay kiss out of an eagerly-waited sitcom episode. Will is frustrated with Jack on how much he wanted to see that kiss and kisses him. Elsewhere Grace confides in Karen about dumping her boyfriend. |
| Guest Cast and Crew : Jo Marie Payton as Mrs. Freeman | Corey Parker as Josh | Jeff Blumenkrantz as Craig Fissay | Al Roker | Mary Pat Gleason as Sally | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : Feb. 22, 2000 |
| Episode 15 - [Advise And Resent] |
| Details : When Will is set up on a blind date by his boss he has internal debates on whether or not to go. Of course Jack gives Will advice on how to be a good blind date. Meanwhile Grace continues to struggle with her wimpy boyfriend Josh as Karen doles out some typically un-wanted advice. |
| Guest Cast and Crew : Jo Marie Payton as Mrs. Freeman | Corey Parker as Josh | Gregory Hines as Ben Doucette | Michael E. Rodgers as Charlie | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : Feb. 29, 2000 |
| Episode 16 - [Hey La Hey La My Ex-Boyfriend's Back] |
| Details : Will thinks that he has another chance with Michael his old boyfriend and Grace's new client. Meanwhile Karen tries taking her career more seriously and asks Grace for greater responsibilities. |
| Guest Cast and Crew : Chris Potter as Michael | Director : James Burrows | Writer : Jeff Greenstein | |
| Air Date : Mar. 14, 2000 |
| Episode 17 - [The Hospital Show] |
| Details : While on a blind date Will finds out that Karen's husband Stan has had a heart attack and rushes to the hospital to be with the gang. Will Jack Grace and Rosario all speculate on who Karen will turn to for her inevitable emotional breakdown. After all who will pay the bills if Stan dies? |
| Guest Cast and Crew : Reggie Hayes as Dr. Osher | Dan Bucatinsky as Neil | Shelley Morrison as Rosario Salazar | Jennifer Elise Cox as Nurse Pittman | Jennie Fahn | Writer : Adam Barr | Director : James Burrows | |
| Air Date : Mar. 28, 2000 |
| Episode 18 - [Sweet And Sour Charity] |
| Details : After winning concert tickets from a radio contest Grace vows to get more involved and she volunteers herself and Will to help out at the community center. Unfortunately her charitable work conficts with the concert. Meanwhile while collecting clothes to give to the mission Jack donates a pair of Karen's most-prized shoes. |
| Guest Cast and Crew : Debra Mooney as Sister Robert | Shelley Morrison as Rosario Salazar | Daryl Sabara as Broccoli Boy | Mary Pat Gleason as Sally | Director : James Burrows | |
| Air Date : Apr. 04, 2000 |
| Episode 19 - [An Affair To Forget] |
| Details : When Rob and Ellen ask Will and Grace to be the best man and maid of honor at their wedding Grace's sexy past with the groom is exposed when Ellen learns at her bachelorette party that Grace once slept with Rob. Meanwhile Jack is confused by his reaction to the entertainment at Rob's bachelor party. |
| Guest Cast and Crew : Leigh-Allyn Baker as Ellen | Gretchen German as Carla / Carl | Tom Gallop as Rob | Steve Paymer as Steve | Writer : Alex Herschlag | Writer : Laura Kightlinger | Director : James Burrows | |
| Air Date : Apr. 18, 2000 |
| Episode 20 - [Girls Interrupted] |
| Details : Despite their history Grace spends a fun evening with Val [ from ep. # 18 Grace Replaced only to have Will suspect her of stealing. Meanwhile Jack becomes attracted to the leader of Welcome Home-an organization for gays who have converted to going straight so he acts straight to woo the man. |
| Guest Cast and Crew : Neil Patrick Harris as Bill | Marianne Muellerleile as Jodie | Molly Shannon as Val Bassett | Writer : Jhoni Marchinko | Director : James Burrows | Writer : Jon Kinnally | Writer : Tracy Poust | |
| Air Date : May. 02, 2000 |
| Episode 21 - [There But For The Grace Of Grace] |
| Details : It's a scary glimpse into the future for Will and Grace when they visit their curmudgeonly retired college professor only to discover that he is a bitter old man that has a Grace of his own. Meanwhile Karen must confront her most mortal enemy the kitchen when Stan requests a homecooked meal for his birthday and she looks to Jack and Ben to come to her rescue. |
| Guest Cast and Crew : Gregory Hines as Ben Doucette | Gary Beach | Piper Laurie | Orson Bean as Professor Joseph Dudley | Director : James Burrows | |
| Air Date : May. 09, 2000 |
| Episode 22 - [My Best Friend's Tush] |
| Details : Grace is thrilled when thanks to Karen's social connections she gets the chance to land a prestigious client for her interior-decorating firm. The only problem? She must compete with international design goddess Helena Barnes. To help boost Grace's confidence Karen assumes the alias of Anastasia Beaverhausen to dig up dirt on the socialite. Meanwhile Jack tries marketing an odd invention: a tush pad for riding the New York City subway. |
| Guest Cast and Crew : Joan Collins | Doug Ballard | Rod Britt | Martin Morales | Writer : Rob Lotterstein | Director : James Burrows | |
| Air Date : May. 16, 2000 |
| Episode 23 - [Ben-Her-Part 1] |
| Details : To help make peace between Grace and Ben Will has them both over to dinner only to have their relationship go beyond friendship. But then Will finds out that Ben is dating someone else. Meanwhile Jack catches Rosario in a clinch with a lover and learns that she wants a divorce. |
| Guest Cast and Crew : Jo Marie Payton as Mrs. Freeman | Corey Parker as Josh | Gregory Hines as Ben Doucette | Shelley Morrison as Rosario Salazar | Writer : David Kohan | Writer : Max Mutchnick | Director : James Burrows | |
| Air Date : May. 23, 2000 |
| Episode 24 - [Ben-Her-Part 2] |
| Details : Forced by his boss to betray both of his friends Will quits--only to discover that everything isn't as it seems. Frustrated he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up. |
| Guest Cast and Crew : Jo Marie Payton as Mrs. Freeman | Corey Parker as Josh | Gregory Hines as Ben Doucette | Shelley Morrison as Rosario Salazar | Director : James Burrows | Writer : Jeff Greenstein | |
| Air Date : May. 23, 2000 |