The best episode written by Alex Herschlag is "Prison Blues", rated 10/10 from 1 user votes. It was "directed by James Burrows". "Prison Blues" aired on 10/18/2001 and is rated 2.0 point(s) higher than their second highest rated, "Anchor Away".
After Stan is arrested for tax evasion, Grace and Karen timidly visit him in prison. Grace is so moved to help her worried friend that she moves right into Karen's deluxe apartment-in-the-sky, where she becomes a demanding guest who's soon hooked on servants, bubble baths and an extravagant lifestyle. Meanwhile, as Stan's attorney, Will struggles with stage-fright when he babbles on during a TV news interview, so Jack convinces him to polish his communication skills by attending an acting class ruled by an imperious teacher.
Director: James Burrows
Writer: Alex Herschlag
In order to land a handsome, gay TV news anchor with a pension for dim, frothy men, Jack convinces Will to not be himself and to act like someone silly and stupid. Karen learns that her alimony will be severely limited unless she can get photos of her ex-husband's affair with Lorraine Finster, so she enlists Grace to go with her to the strip club where Lorraine works. Olympian Adam Rippon has a cameo as a barista with an attitude.
Director: James Burrows
Writer: Alex Herschlag
When Adam gets fed up with endless demands from his daughter's kindergarten teacher, Mrs. Rodriguez, he makes a hasty decision that lands him in hot water with his wife Andi.
Director: James Burrows
Writer: Alex Herschlag
Adam and Andi are shocked when they finally meet Lowell's wife, Jen.
Director: Pamela Fryman
Writer: Alex Herschlag
When Adam and Andi have the dreaded 'talk' with Teddy and Kate, their awkward approach makes the kids horribly uncomfortable.
Director: Pamela Fryman
Writer: Alex Herschlag
Grace's visiting mom, Bobbi Adler, a would-be star whose propensity for breaking out into show tunes and impressions dismays her daughter – and delights Will, Jack and Karen – wreaks havoc by suggesting Will and Grace wed, despite their sexual differences. When Will winces at the fantasy of committing to anyone who needs to be the star of a relationship, Grace realizes she's more of a chip off the old block than she imagined.
Director: James Burrows
Writer: Alex Herschlag
When Rob and Ellen admit that they don't have fun playing games with Will and Grace because of Grace's competitive nature, Grace works to change her image. However, as Grace loses her competitive edge, Will's emerges and he convinces his partner to care only about winning. Meanwhile, after learning how to administer CPR from Jack, Karen saves a workman's life.
Director: James Burrows
Writer: Alex Herschlag
When Victoria wants to turn her cancelled soap opera into an app, she has to get the series creator on board. They enlist the cast, including the actor who played Honor St. Ravens ex-husband, to film a new episode picking up where the finale left off.
Director: N/A
Writer: Alex Herschlag
Will gives local newscaster McCoy Whitman a second chance and, with the help of Jack, finally gets to know the man behind the newsman. Grace's campaign for Design Guild President hits a snag when the deciding vote comes down to her old nemesis, Val. Karen acts as Grace's campaign manager, and attempts to secure Val's vote by any means necessary.
Director: James Burrows
Writer: Alex Herschlag
Jackie's sister and outrageously wealthy brother-in-law move in after the couple's money dries up.
Director: Victor Gonzalez
Writer: Alex Herschlag
When Rob and Ellen ask Will and Grace to be the best man and maid of honor at their wedding, Grace's sexy past with the groom is exposed when Ellen learns at her bachelorette party that Grace once slept with Rob. Meanwhile, Jack is confused by his reaction to the entertainment at Rob's bachelor party.
Director: James Burrows
Writer: Alex Herschlag