Will and Grace (1998) Season 5 Episodes

Find out where to watch Season 5 of Will and Grace (1998) tonight
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Season 5 Episode Guide

Episode 1 - ...And the Horse He Rode in On

Continuing from the season finale in the year's first new episode, Grace is rescued by a handsome Jewish doctor (guest star Harry Connick Jr.) who pulls her up on his horse and delivers her just in time for her insemination with an impatient Will.

  

Episode 2 - Bacon and Eggs

After stalking actor Kevin Bacon (guest-starring as himself), Jack (Sean Hayes) lands his dream job when the unsuspecting celebrity hires him as his personal assistant and immediately assigns him to find out who's been harassing him.

  

Episode 3 - The Kid Stays Out of the Picture

Grace is so entranced by her romantic relationship with a handsome doctor that she asks Will for an extra month to re-consider her commitment to conceiving their child through artificial insemination -- resulting in a verbal sparring match.

  

Episode 4 - Humongous Growth

While Will (Eric McCormack) and Grace (Debra Messing) are feuding, Karen and Jack hatch a wobbly plan to patch up their differences about not co-parenting a baby by tricking each one into attending the same child's birthday party.

  

Episode 5 - It's the Gay Pumpkin, Charlie Brown

On Halloween, Grace allows her new beau Leo (guest star Harry Connick Jr.) to drag her into the rustic fall countryside for a long and scary bike ride -- along with a reluctant Will and his newfound friend.

  

Episode 6 - Boardroom and a Parked Place

Will's (Eric McCormack) budding interest in a fellow lawyer in his office is nipped upon the arrival of his firm's aggressive new boss (guest star Gene Wilder, "Young Frankenstein"), who whips the troops into shape and orders Will to fire his friend.

  

Episode 7 - The Needle and the Omelet's Done

When Grace accompanies Leo to dinner with some "friends," she doesn't realize that he's tricked her and instead introduced her to his real parents -- and she soon regrets her earlier salty dialogue and suggestive attitude

  

Episode 8 - Marry Me a Little, Marry Me a Little More Part 1

After Grace (Debra Messing) impulsively accepts a marriage proposal from Leo there seem to be a million roadblocks between her and an actual wedding, not the least of which is her best friend Will's (Eric McCormack) unease about the whole idea.

  

Episode 9 - Marry Me a Little, Marry Me a Little More Part 2

After Grace (Debra Messing) impulsively accepts a marriage proposal from Leo there seem to be a million roadblocks between her and an actual wedding, not the least of which is her best friend Will's (Eric McCormack) unease about the whole idea.

  

Episode 10 - The Honeymoon's Over

After a displaced Karen (Megan Mullally) is booted from her Palace Hotel digs, a sympathetic Will (Eric McCormack) agrees to let her move in with him -- at least until she turns his apartment into a federal disaster zone with her exorbitant lifestyle

  

Episode 11 - All About Christmas Eve

On Christmas Eve, Grace (Debra Messing) is torn when she has only two tickets to "The Nutcracker" musical and can't take both her best friend Will (Eric McCormack) and new husband Leo (guest star Harry Connick Jr.).

  

Episode 12 - Field of Queens

When Jack convinces tangle-footed Will to join him on a gay soccer team, Will's inept play leaves him warming the bench -- which allows him to bond with teenaged Elliot who also is the last man called upon with his own youth soccer team.

  

Episode 13 - Fagmalion Part I: Gay It Forward

Grace (Debra Messing) is puzzled over what to make of her strange bohemian neighbor (guest star Rosanna Arquette, "Pulp Fiction") when she moves into Leo's Brooklyn digs.

  

Episode 14 - Fagmalion Part II: Attack of the Clones

Picking up where we left off last week, Will and Jack continue their campaign to adapt Karen's awkward cousin to his new way of life -- but their flamboyant efforts to help him only remind Will of his own clumsy experiences when he came "out".

  

Episode 15 - Homojo

Jack (Sean Hayes) suffers Karen's (Megan Mullally) wrath when he is seduced into friendship with her manipulative British romantic rival (guest star Minnie Driver, "Good Will Hunting"), who has set up house with Karen's ex-husband.

  

Episode 16 - Women and Children First

Jack (Sean Hayes) reconnects with his childhood babysitter (guest star Demi Moore, "A Few Good Men") and falls back into childhood patterns, befuddling Will (Eric McCormack).

  

Episode 17 - Fagmalion Part III: Bye, Bye, Beardy

Will and Jack'stransformation of Karen's schlubby cousin Barry is complete -- but his coming-out party leaves Will with mixed emotions about his new "creation," prompting some unwanted advice from Grace.

  

Episode 18 - Fagmalion Part IV: The Guy Who Loved Me

A jealous Will keeps a wary eye on the re-modeled Barry when he spies him disappearing with Jack while Karen switches roles with Rosario and pretends to be a maid in order to court a handsome maintenance worker (guest star Bruno Campos).

  

Episode 19 - Sex, Losers, and Videotape

Still nursing a grudge over his last failed relationship, Will forms a gin-soaked anti-romance club with other lovelorn losers, Mr. Stein, and Karen -- but the threesome shrinks dramatically when Stein takes a shine to the ever-ready Karen.

  

Episode 20 - Leo Unwrapped

Will's attempt to orchestrate a surprise for Grace's birthday by sneaking Leo back from Africa fails when Leo arrives earlier than expected -- and after Grace bumps into Leo, they agree to an elaborate charade to keep Will's "surprise" intact.

  

Episode 21 - Dolls and Dolls

In search of a roommate, Karen (Megan Mullally) finds instant karma with a peculiar yet high-maintenance office worker (guest star Madonna) who happily shares many of Karen's eccentricities -- including her taste in men.

  

Episode 22 - May Divorce Be With You

Will reluctantly opposes Karen when he represents her husband while she hires a goofy, immature young man (guest star Macaulay Culkin, "Home Alone") who seems barely out of high school to argue her case -- and Will takes pity on the pseudo-slacker.

  

Episode 23 - 23

Karen learns that ex-husband Stan has suddenly passed away, and the funeral becomes a contest of wills between Karen and her British rival -- and a free-for-all when the will is read for everyone who ever felt deserving, such as Will.

  

Episode 24 - 24

In the season finale, Karen confronts her ex-husband's mistress (guest star Minnie Driver, "Good Will Hunting") before she invites Will (Eric McCormack), Grace (Debra Messing) and Jack (Sean Hayes) on her extravagant yacht for a somber ceremony.

  



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