... And the Horse He Rode in On
Season 5, Episode 1 Unrated
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Continuing from the season finale in the year's first new episode, a dazed Grace (Debra Messing) 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 (Eric McCormack). But their new relationship as expectant parents puts a strain on Will and Grace's relationship when they agree not to date until their baby is born. Meanwhile, a restless Karen (Megan Mullally) can't make up her mind about cheating on her imprisoned husband with the genteel but ardent suitor Lionel (guest star Rip Torn). Sean Hayes also stars.
Bacon and Eggs
Season 5, Episode 2 Unrated
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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. Elsewhere, while Will (Eric McCormack) and Grace (Debra Messing) wait for the right color to appear on their home pregnancy test, Grace is visited by a handsome doctor (guest star Harry Connick Jr.) who makes her a tempting offer. In addition, Karen (Megan Mullally) looks for a way out of her on-again, off-again relationship with the courtly and irresistible suitor Lionel (guest star Rip Torn). Shelley Morrison also stars.
The Kid Stays Out of the Picture
Season 5, Episode 3 Unrated
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Grace (Debra Messing) is so entranced by her budding romantic relationship with a handsome doctor (Grammy-winning guest star Harry Connick Jr.) that she asks an impatient Will (Eric McCormack) for an extra month to re-consider her commitment to conceiving their child through artificial insemination - resulting in a verbal sparring match. Megan Mullally and Sean Hayes also star.
Humongous Growth
Season 5, Episode 4 Unrated
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While Will (Eric McCormack) and Grace (Debra Messing) are feuding, Karen (Megan Mullally) and Jack (Sean Hayes) 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. After arguing over who brought the better gift, the feathers continue to fly as the best friends fuss over their conflicting agendas.
It's the Gay Pumpkin, Charlie Brown
Season 5, Episode 5 Unrated
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On Halloween, Grace (Debra Messing) 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 (Eric McCormack) and his newfound friend (guest star Jason Marsden) - but she finds that she can't pretend to be the outdoorsy type just to please her man. Meanwhile, Jack (Sean Hayes) coaxes Karen (Megan Mullally) into attending a gay men's therapy session when she feels slight - very slight - pangs of marital guilt over her earlier attraction to the courtly suitor Lionel.
Boardroom and a Parked Place
Season 5, Episode 6 Unrated
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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 - until Will discovers the real reason behind the false bravado. Meanwhile, Grace (Debra Messing) and Jack (Sean Hayes) are shocked to discover that their highfalutin' pal Karen (Megan Mullally) is now poorer than a church mouse - and living in her limo. Shelley Morrison also stars.
The Needle and the Omelet's Done
Season 5, Episode 7 Unrated
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When Grace (Debra Messing) accompanies Leo (guest star Harry Connick Jr.) 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. Elsewhere, Jack (Sean Hayes) is again confronted by Zandra (guest star Eileen Brennan, "Private Benjamin") - his gruff acting teacher - when he tries to showcase his meager talent in a class while a willing Will (Eric McCormack) joins Karen (Megan Mullally) in subjecting to a Botox facial injection.
Marry Me A Little, Pt. 1
Season 5, Episode 8 Unrated
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After Grace (Debra Messing) impulsively accepts a marriage proposal from Leo (guest star Harry Connick, Jr.), 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. Sean Hayes, Megan Mullally and Shelley Morrison also star; Debbie Reynolds and Katie Couric (NBC's "Today") guest-star. Part 1 of 2.
Marry Me A Little More, Pt. 2
Season 5, Episode 9 Unrated
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After Grace (Debra Messing) impulsively accepts a marriage proposal from Leo (guest star Harry Connick, Jr.), 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. Sean Hayes, Megan Mullally and Shelley Morrison also star; Debbie Reynolds and Katie Couric (NBC's "Today") guest-star. Part 2 of 2.
The Honeymoon's Over
Season 5, Episode 10 Unrated
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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, forcing Will to try and unload her onto Grace's (Debra Messing) shoulders. Meanwhile, Jack (Sean Hayes) loses style points when he poses incognito out of fear that the "Gay Mafia" has it out for him. Grammy-winning superstar Elton John plays himself as an omniscient "Gay Mafia" figurehead.
All About Christmas Eve
Season 5, Episode 11 Unrated
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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.) - but her back-and-forth indecision leaves Will spinning like a Hanukkah dreidel between a dithering Grace and his previous holiday plans with Jack (Sean Hayes) and Karen (Megan Mullally). Mary McDonough ("The Waltons") guest-stars.
Field of Queens
Season 5, Episode 12 Unrated
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When Jack (Sean Hayes) convinces tangle-footed Will (Eric McCormack) 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 ((Michael Angarano) who also is the last man called upon with his own youth soccer team. Meanwhile, Grace (Debra Messing) is delighted that Karen (Megan Mullally) is giddy in anticipation of her date with a handsome restaurant owner (guest star Andy Garcia, "Ocean's Eleven").
Fagmalion, Pt. 1: Gay It Forward
Season 5, Episode 13 Unrated
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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. Sean Hayes and Megan Mullally also star.
Fagmalion, Pt. 2: Attack of the Clones
Season 5, Episode 14 Unrated
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Picking up where we left off last week, Will (Eric McCormack) and Jack (Sean Hayes) continue their campaign to adapt Karen's (Megan Mullally) awkward cousin (guest star Dan Futterman, "Enough") 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" in 1986. Elsewhere, Grace (Debra Messing) feels abandoned by Leo (guest star Harry Connick Jr.) when he leaves for three weeks to offer his medical services to the needy in Africa.
Homojo
Season 5, Episode 15 Unrated
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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. Meanwhile, Will (Eric McCormack) and Grace (Debra Messing) try to re-connect their lagging friendship with a competitive night of board games with their friends.
Women and Children First
Season 5, Episode 16 Unrated
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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). Meanwhile, Grace (Debra Messing) has a girl's night out in Brooklyn with Karen (Megan Mullally), Rosario (Shelley Morrison), Ellen (guest Leigh-Allyn Baker) and new neighbor Julie (guest star Rosanna Arquette) and offends Karen when she doesn't take her advice regarding Leo.
Fagmalion, Pt. 3: Bye, Bye, Beardy
Season 5, Episode 17 Unrated
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Will (Eric McCormack) and Jack's (Sean Hayes) transformation of Karen's (Megan Mullally) schlubby cousin Barry (guest star Dan Futterman, "Enough") is complete - but his coming-out party leaves Will with mixed emotions about his new "creation," prompting some unwanted advice from Grace (Debra Messing). In another corner, Karen duels with her flamboyant rival Beverley (guest star Leslie Jordan) in a war of wills during a silent auction for charity.
Fagmalion, Pt. 4: The Guy Who Loved Me
Season 5, Episode 18 Unrated
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A jealous Will (Eric McCormack) keeps a wary eye on the re-modeled Barry (guest star Dan Futterman, "Enough") when he spies him disappearing with Jack (Sean Hayes) while Karen (Megan Mullally) switches roles with Rosario (Shelley Morrison) and pretends to be a maid in order to court a handsome maintenance worker (guest star Bruno Campos). Meanwhile, Grace (Debra Messing) finds herself hanging out more and more in her old digs in Will's apartment as she waits for her husband to return from overseas.
Sex. Losers & Videotape
Season 5, Episode 19 Unrated
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Still nursing a grudge over his last failed relationship, Will (Eric McCormack) forms a gin-soaked anti-romance club with other lovelorn losers - his cuckoo boss, Mr. Stein (guest star Gene Wilder, "The Producers"), and Karen (Megan Mullally) - but the threesome shrinks dramatically when Stein takes a shine to the ever-ready Karen. Meanwhile, Jack (Sean Hayes) sneaks a video camera into Grace's (Debra Messing) private boudoir and records her privates - and posterior - for posterity.
Leo Unwrapped
Season 5, Episode 20 Unrated
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Will's (Eric McCormack) attempt to orchestrate a surprise for Grace's (Debra Messing) birthday by sneaking Leo (guest star Harry Connick Jr.) back from Africa deflates like so many birthday balloons when Leo arrives earlier than expected - and after Grace bumps into Leo, they agree to an elaborate charade to keep Will's "surprise" intact. Meanwhile, Grace recruits Jack (Sean Hayes) and Karen (Megan Mullally) to keep Leo out of the way until the appointed time but they take their mission too seriously.
Dolls and Dolls
Season 5, Episode 21 Unrated
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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. Meanwhile, when Will (Eric McCormack) falls off his clogs and twists an ankle, he develops a habit of taking too many painkillers, prompting a concerned Grace (Debra Messing) and Jack (Sean Hayes) to intervene and interfere.
May Divorce Be With You
Season 5, Episode 22 Unrated
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Will (Eric McCormack) reluctantly opposes Karen (Megan Mullally) 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. Elsewhere, Grace (Debra Messing) hires Jack (Sean Hayes) to temporarily replace Karen but finds she might have to choose between her friendship with him and a wealthy client (guest star Clark Gregg). Shelley Morrison also stars.
23
Season 5, Episode 23 Unrated
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In the middle of her divorce proceedings, Karen (Megan Mullally) learns that ex-husband Stan has suddenly passed away, and the funeral becomes a contest of wills between Karen and her British rival (guest star Minnie Driver, "Good Will Hunting") - and a free-for-all when the will is read for everyone who ever felt deserving, such as Will (Eric McCormack). Meanwhile, Grace (Debra Messing) is shocked when recently returned husband Leo (guest star Harry Connick Jr.) is called back into service for a charitable medical organization overseas and asks her to make the trip with him. Sean Hayes and Shelley Morrison also star.
24
Season 5, Episode 24 Unrated
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In the season finale, Karen (Megan Mullally) 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. While Grace goes into a jealous fit when she meets the sexy co-worker (guest star Nicolette Sheridan, "Knots Landing") of her husband Leo (Harry Connick Jr.). Singer Deborah Harry also guest-stars as herself in the episode. Shelley Morrison also stars.
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