Macaulay Culkin finally broke from his child star past on Will & Grace

Culkin’s role as a duplicitous lawyer reminded viewers that he had charisma, screen presence, and acting chops to spare

By Gwen Ihnat  |  August 11, 2021 | 5:00am

Image: Screenshot: Will & Grace TV Features Will & Grace

Will & Grace, “May Divorce Be With You,” season five, episode 22 (2003)

When Will & Grace debuted on NBC in 1998, it broke ground as one of the first TV series with gay lead characters, a year after Ellen DeGeneres came out in “The Puppy Episode” on Ellen. Part of the sitcom’s success—leading to its original Emmy-winning eight seasons—lay its economical casting: four, tightly connected leads consisting of two gay men and two straight women—Will (Eric McCormack), Grace (Debra Messing), Jack (Sean Hayes), and Karen (Megan Mullally). This also opened up a lot of space for guest-star appearances, and soon having a parade of famous people show up as love interests, relatives, or co-workers became almost as much of a draw of the series as the four leads themselves. Woody Harrelson had a memorable impact as a love interest of Grace’s, as did John Cleese with Karen. Debbie Reynolds was nominated for an Emmy for her turn as Grace’s mom. Gene Wilder won an Emmy for playing Will’s eccentric boss, as did Bobby Cannavale as Will’s eventual husband. Such was the show’s eventual zeitgeist popularity that sometimes stars eager to guest on the show would just appear as themselves, like Kevin Bacon performing the Footloose dance with Will, Jennifer Lopez poking fun at her diva image, or Cher slapping Jack and telling him to snap out of it, Moonstruck-style.

Besides possible awards recognition or the chance to show up on a buzzy TV series, appearing in a guest star role also affords a performer the opportunity to appear in a different light. Few actors made better use of their Will & Grace guest-star appearance than Macaulay Culkin. In 2003, Culkin had been out of the limelight for almost 10 years. After Home Alone (1990) made him the most popular child actor in decades, Culkin followed up the unexpected blockbuster with a sentimental turn in My Girl (1991) and a homicidal one in The Good Son (1993). But by 1994, Culkin released lackluster movies like Getting Even With Dad and Richie Rich, and it was clear that the then-14-year-old was burned out, especially as the horrific acts of his stage father Kit made headlines in Culkin’s parents’ contentious divorce. It was only through court documents that young Culkin realized he was worth $50 million.

Macaulay Culkin returned to acting in 2000 with a well-received stage turn in Madame Melville in New York, but 2003 marked his first screen appearances since 1994, aside from a few music videos. On the big screen, Culkin played as far away from type as he could possibly get as the title character in Party Monster, the story of club kid Michael Alig, who murdered and dismembered his friend/drug dealer. Culkin’s small screen return was much more palatable: an appearance in the 22nd episode of Will & Grace’s fifth season, “May Divorce Be With You.”

In the episode, when Will can’t represent Karen in her divorce settlement because her husband Stan is a client of his firm, Karen goes out and hires J.T. (Culkin) instead. He was 23 at the time, but as boyish as ever: The joke of the episode is that Karen is placing all her hopes on this apparently inexperienced lawyer who wears a too-big suit from Men’s Wearhouse and is psyched because his mom put a Kudos bar in his lunch. Will tries to talk Karen out of retaining J.T.; then when an overwhelmed J.T. comes to Will asking for help, Will sympathetically steers the younger man toward the evidence necessary to win Karen’s case.

Karen’s next meeting with J.T. is at a fast-food place (“I guess this is where you meet a lawyer on retainer who still wears a retainer”), and Will once again pleads with her to hire a more experienced barrister. After Will leaves, Karen tries to fire J.T. and pours herself a shot. In a stunning role reversal, J.T. grabs the shot glass and downs it himself. He reveals that he’s been playing Will with his lost little boy act and will use the evidence Will helped him secure to crush him in court. J.T. then starts bragging about how he has a Mercedes and how Deborah Harry thanked him for a previous similar settlement by “rocking my world” in the back of it. Karen’s reaction—and that of the live studio audience—is palpable. This guy may still look like Kevin McAllister, but he’s all grown up, a status secured when Karen fans herself and says, “Oh my… how would you like to live under my skirt?” With that one bawdy line, Macaulay Culkin makes the leap from child actor to adult actor, underlined when he tosses some cash at Karen to go get herself a bikini wax (“I like a clean work space”). Not only was Culkin an adult, but an actual sexual being: It was a jarring transformation.

The episode is fun, offering lots of one-liners poking fun at J.T.’s age, with Will speculating that J.T.’s previous cases included Bert V. Ernie and that he purchased his power suit at Osh Kosh B’Gosh. But the real draw is Culkin’s double play—the transformation from the aw-shucks kid to the corporate shark. The performance was an effective reminder that his huge popularity in the prior decade was no accident: He always had charisma, a commanding screen presence, and an abundance of acting talent. Culkin easily slid into the rhythm of Will & Grace’s witty one-liners, and had tangible chemistry with the always-great Mullally. The episode’s B-plot, in which Jack wants Grace to quit working with his rich ex-boyfriend (Clark Gregg), pales in comparison.

Similar to actors like Daniel Radcliffe, Elijah Wood, and Robert Pattinson, Macaulay Culkin made enough money at a young age—even with all the drawbacks that came with such immense fame: “It’s hard for me to remember a time when people weren’t staring at me for one reason or another,” he told New York Magazine in 2001—that he is able to pick only the projects he really wants to work on. To date, those roles have included a paraplegic in the religious-themed dark teen comedy Saved!, hanging out with his Party Monster co-star Seth Green on Robot Chicken, and playing himself as a barista on The Jim Gaffigan Show. Later this month, the now 40-year-old (and new father) Culkin will join Ryan Murphy’s usual roster of players, along with his goddaughter, Paris Jackson, in the 10th season of American Horror Story, titled Double Feature. Murphy told Entertainment Weekly that one of the lures he offered to Culkin was that his character would have “crazy, erotic sex with Kathy Bates”; Culkin agreed immediately. “There’s both a lightness and a darkness with Macaulay Culkin that I’m attracted to,” Murphy said of the actor. The first time Culkin showed both of those sides as an adult actor was on Will & Grace, a perfect case of taking full advantage of a random guest spot to showcase a different aspect of the performer we thought we knew.