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)

Will presents his newly reconciled parents with a cruise for their anniversary, but their individual secrets ruin his hopes.

When Grace and Leo join Karen for a friendly game of tennis at her exclusive club, her fierce playing style sends Grace fleeing the court. However, when the reason for her angry play is her hatred for Leo, Grace is determined to find a way for them to get along. Elsewhere, a nervous Will suckers Jack into visiting his depressed mother in Connecticut hoping they can cheer her up.

Earning a brief speaking role in an off Broadway play, Jack shares the stage with legendary actor James Earl Jones. However, when the play's director rejects James' performance in favor of Jack's one-line triumph, the award-winning actor looks to his co-star for instruction - enrolling in the McFarland acting school. Meanwhile, new roommates Will and his mother Marilyn continue their living arrangement, despite a secret desire to part ways.

Continuing his new role as caretaker for a disabled Marilyn, a resentful Will takes his wheelchair-bound mother for an afternoon roll in the park and bumps into an attractive bachelor Tom wheeling an invalid of his own. Using his mother as a reason for a daily rendezvous in the park, Will attempts to build up the courage to ask Tom out. Elsewhere, Karen continues her lifelong quest to hunt down hubby-stealing Lorraine tracking her to a room at the Peninsula hotel only to discover occupant to be her father Lester.

Responding to the pleas of his father's mistress-turned-girlfriend Tina, Will attempts to discover whether there is a new woman in his dad's life. However, when his father's new mistress turns out to be his mother, Will must find a way to break the shocking truth to Tina. Meanwhile, Elliot's decision to try out for his high school cheerleading squad has Jack all smiles as he is determined to help his son make the team.

Grace attends a holiday party at Will's mother Marilyn's home and accidentally breaks a treasured Lladro figurine. Will convinces Grace not to tell his mother and to blame the accident on one of the other guests at the party. Elsewhere, Karen's stepdaughter, Olivia, comes to stay for the Christmas holiday. While lunching at the mall they start making fun of people, but Karen's remarks are especially mean and Olivia and her friends take offense.

After a near-death experience in a Jean Boutique, Grace decides to write her will and enlists Will's legal expertise to make sure she's fair when bequeathing her money. Grace visits Will's mother to find out how much Will plans to leave her and is shocked by what she finds. Thanks to Grace, Will also takes a look at his life and decides it's time to make a life altering career move. Meanwhile, Jack and Karen find an imposter teaching Jack's ""McFarland Method Of Acting."" Realizing he needs new material to get back into teaching, Jack changes his method to win back his students.

While spending the holidays at Will’s mother Marilyn’s house, Grace gets cozy with Will’s brother and old flame Sam. Sam’s adopted daughter finds a fan in Karen, who is intrigued by the little girl.

After losing his job as the host of "JackTalk," Jack vows never to return to acting. An unrelenting Karen, however, will not let Jack give up on his passion and decides to do whatever it takes to get Jack to an audition.

Friends and family gather for the funeral of Will's father. At the reception everyone shares with Will fond last memories of his father, while Will's last memory of his father is not as pleasant. Marilyn helps him realize the changes needed in his life.