A.I.: Artificial Insemination is the two-part season finale of the fourth season, the 26th & 27th episode of the season and 92nd episode overall.
The first part deals with Will and Grace's decision to have a baby. The second part deals with each of the main characters facing dilemmas about the future of their families and career.
Will and Grace's familyWill and Grace try to keep their plan of starting a family a secret from Jack and Karen but soon find out they each have told the other anyway. At their first try at IVF the bag containing Will's sperm gets mixed up and Rosario ends up mopping the floor with Will's sperm. After another failed attempt, they try to get Grace pregnant naturally but could not push through because Will is gay and according to Grace, "sex changes things", including their friendship.
On their way for another try at the fertility clinic, the taxi they are in breaks down so Grace runs through Central Park with Will's sperm to make it to their appointment but is distracted by Jack and she runs into a lamp post, knocking herself out. She wakes up to the silhouette of a man in a horse.
While celebrating in his new office, he gets knocked out by falling boxes and dreams about God encouraging him to follow his bliss, which is still performing. Jack wakes up with an epiphany to quit his job at Barney's and try out for another audition instead.
Karen has been lonely since her husband Stanley went to prison. A charming rich man named Lionel Banks approaches her at a hotel bar and propositions her, mistaking her for a prostitute. When he asks Karen if she is married, she lies and tells him she is not. She eventually admits that she is married however Lionel says that he does not care and then hands her the key to his suite before leaving. Karen feels tempted to follow him.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Shelley Morrison (Rosario Salazar)
- Cher (Herself)
- Rip Torn (Lionel Banks)
- Harry Connick, Jr. as Leo Markus
- Laura Kightlinger (Nurse Sheila)
- J Lucas (Ruben)
- Andrew Rosenbach (Terry)
- Charles C. Stevenson Jr (Smitty)
- Peggy Lane O'Rourke (Female Cabbie)
- Richard Assad (Male Cabbie)
- Jack's old boss Dorleen is mentioned getting fired after going to rehab.
- Jack does her impression of Cher again as he wakes up from his dream.
- Lionel introduces himself as "Lionel, like the train", after the Lionel brand of toys who manufactured trains during the 1990s. Karen introduces herself using her alias Anastasia Beaverhausen, which according to her "Anastasia, like Russian royalty", referring to the legendary Grand Duchess Anastasia.
- Will jokes that Mia Farrow has 4 billion of the world's population, poking fun at the actress' 11 children, 7 of which were adopted from different nations.
- Karen tries to cover her affair with Lionel Banks by saying he is the bass player of her Lynyrd Skynyrd tribute band, famous for their song Sweet Home Alabama.
- Rosario orders P'Zone, the pizza calzone offered by Pizza Hut.
|Jack:||I was up all night thinking about what my new calling in life should be. There's been quite a void since I abandoned my acting career.|
|Will:||I thought your acting career was the void.|
|Lionel:||You have a very delightful chuckle.|
|Karen:||Oh, thank you. They're real, too.|
Where did you come from, Lionel? Did the Smooth-Talking Gigolo Convention let out early? — Karen
|Lionel:||You don't have sex for money?|
|Karen:||No, I do not! For jewels, for furs, for mixed securities, like a lady! But for money? How dare you!|
You better get down to women's shoes, pronzo. It's a festival of tears and queers down there. — Ruben