Will & Grace Season 4 Episode 4 Prison Blues

Will & Grace Season 4 Episode 4, Prison Blues, is a hilarious episode that sees Grace landing in jail. In this episode, the duo receives an unexpected phone call from Will's malevolent ex-boyfriend Vince, who is currently behind bars. He invites them to visit him in prison, which they reluctantly do. However, things take a drastic turn when Grace accidentally steals a pack of cigarettes from the commissary while trying to help Vince, which sees her being arrested and sent to jail.

The episode takes place largely within the jail, with Grace struggling to come to terms with her newfound surroundings while a bewildered Will tries to figure out a way to bail her out. While in jail, Grace has to deal with the harsh realities of prison life, as she's forced to share a cell with an intimidating inmate named Regina (played by the legendary Rosie O'Donnell). Regina is rough around the edges, but quickly takes Grace under her wing, teaching her the lay of the land within the prison walls.

Meanwhile, Will is left to figure out how to get Grace out of jail, enlisting the help of his flamboyant assistant, Jack. Together, they hatch a plan to bribe the judge handling Grace's case, but quickly realize that pulling off such a shady scheme won't be easy.

One of the standout moments of the episode is the hilarious interaction between Grace and Regina. Despite completely opposing personalities, the two quickly develop a friendship that's funny, heartwarming, and entirely unexpected. Rosie O'Donnell is a scene-stealer in her role, perfectly embodying the tough-talking Regina with apparent ease. The chemistry between Debra Messing and O'Donnell is palpable, and their scenes together are some of the best in the entire episode.

Another highlight of Prison Blues is the scenes between Will and Jack, who are up to their usual hijinks as they try to come up with a plan to free Grace. Sean Hayes as Jack, in particular, shines in this episode, providing plenty of laughs with his over-the-top antics and flamboyant personality.

Overall, Will & Grace Season 4 Episode 4, Prison Blues, is a standout episode of the series. It's funny, heartwarming, and features some fantastic performances from the entire cast. The jail setting adds a unique twist to the familiar formula of the show, and the chemistry between the characters ensures that there's never a dull moment. Whether you're a longtime fan of the series or a newcomer, this episode is not to be missed.