Grace in the Hole is the 14th episode of the fourth season and 85th overall.
While visiting Stan in prison, Grace bumps into an old crush from high school named Glenn Gabriel. They flirt and he woos her by saying that he also had a crush on her and that whenever his band from high school sang Toto's Rosanna, he was really singing it to Grace. After she gives him her number, she finds out he is a prisoner.
With Grace's help, Will serves as Glenn's attorney at his trial. Grace then finds out that Glenn is seeing other women while in prison, saying to them the same things he had said to her.
Rosario's prison challenge
When Karen dismisses the idea of visiting her husband in prison, Rosario challenges her and Jack that if they could not stand three days as "prisoners" in her bedroom, Karen must visit Stan in prison everyday for a month.
The challenge gets frustrating for Karen and two hours before winning, she concedes, finally concerned at how things must be for Stan in an actual prison.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Kirk Baltz (Glenn Gabriel)
- Brent Sexton (Guard)
- Cheryl Bricker (Sheila Slovinsky)
- Steven Shaw (Judge)
- Title of the episode is a play on the phrase "ace in the hole", and an allusion to "the hole" meaning solitary confinement.
- Glenn Gabriel sings Toto's Rosanna (1982) to girls to deceive them into helping him. It has been a popular assumption that the song was written about actress Rosanna Arquette who was dating Toto keyboardist Steve Porcaro. Arquette later appears as Julie, Grace's Brooklyn neighbor in season 6.
- This is the second time that Grace walked out of a scene being similar to what she claimed not to be. In this episode after she dismisses Will's description of her being "one of those women in a polka-dot dress and a floppy hat that bakes brownies for serial killers", she walks out in a polka-dot dress with a big hat and pastry for Glenn in jail. In The Unsinkable Mommy Adler, Will describes her as a "star" and she walks out of a restaurant with her coat on her shoulders, a scarf around her neck, big shades, and her nose in the air.
- While in "prison", Karen and Jack sing The Chordettes' Mr. Sandman (1954).
- Sheila Slovinsky's last name came from crew member Zack Slovinsky, who would later co-write the episode Partners 'n Crime.
- Jack asks the prison guard if Robert Downey is in there, a reference to Downey's reputation during the late 1990s after he was arrested multiple times.
- Rosario calls Jack and Karen "Dumb and Drunker", after the film Dumb and Dumber (1994).
- After Karen asks if she should take her top off, Rosario also calls Karen "Gypsy Rose Lush" referencing burlesque actress Gypsy Rose Lee and Karen's alcoholism.
- Will asks if Glenn, who was in a Jewish gang, was a "Bloodberg" or "Cripstein". This is an allusion to California gangs Bloods and Crips, with appended -berg and -stein popular among Jewish last names.
- When asked if she will be visiting Stan in prison, Karen says she would rather watch American director Woody Allen "get it on with his daughter-wife" Soon-Yi, the adoptive daughter of Allen's former partner Mia Farrow. Allen married Soon-Yi in 1997 and they live in New York City. In Grace, Replaced, Jack finds Soon-Yi's phone bill.
- Jack mentions learning about suffering from "from the Dalai Lama by way of Richard Gere". American actor Richard Gere has met with and is a supporter of the Dalai Lama.
- In describing Grace's relationship with Glenn, Will refers to popular prison films The Shawshank Redemption (1994), Jailhouse Rock (1957), Cool Hand Luke (1967).
- To prepare for his litigation, Will gets Paul Newman's half-glasses from his role in The Verdict (1982). He also learned moves from courtroom dramas The Firm (1993), A Few Good Men (1992), and does an impression of Tom Cruise in Jerry Maguire (1996).
- After the hearing, Grace refers to Will using famous lawyers: Oliver Wendell Homo (Oliver Wendell Holmes, Jr.), F. Lee Gay-ley (F. Lee Bailey) and Johnnie Cock-ran.
|Grace:||In high school, he was so weird and cool. He was in a Jewish gang.|
|Will:||What is that, exactly? They drive by and slash your credit rating?|
|Grace:||He's not a convict. He is just some guy who did some white collar real estate thing and needs to be behind bars for a little while until he learns his lesson.|
|Will:||Oh. Hey, he wouldn't happen to have a brother who's not gay but likes to have sex with men, does he?|
Thanks to you, we missed our show. What if Martha Stewart was nice today? — Jack
|Grace:||I hate men.|
|Will:||Good. More for me.|
I feel like an animal caught in a trap! Oh, now I miss my coats, damn it. — Karen