The best celebrity cameos on Will & Grace over the years

Alec Baldwin as Malcom (Appearance: S8, E1):

Alec Baldwin starred in one episode of Will & Grace as Malcom, Will’s boss who revealed to Will (Eric McCormack) that Karen’s (Megan Mullally) husband Stan was still alive. Alec’s performance was even better because this particular episode was filmed live to celebrate the final season of the show back in 2007.

Demi Moore as Sissy Palmer-Ginsburg (Appearance:S5, E16):

Demi Moore starred as Jack’s (Sean Hayes) childhood babysitter in a 2003 episode of W&G. Despite the years that had passed, Demi’s character Sissy was still very much stuck in her babysitting days. Jack decided to hire Sissy to babysit him again but it ended quickly when he realised how expensive her services were!

Macaulay Culkin as Jason Towne (Appearance: S5, E22):

One of the most famous child stars of all time, Macaulay Culkin appeared as Karen’s divorce attorney in season five of W&G. Will was worried when Karen hired the baby-faced lawyer Jason, who appeared to be a bumbling kid in a suit. But it turned out that it was all an act and Jason acted this way in order to trick Will into going easy on him!

Minnie Driver as Lorraine Finster (Appearance: reoccurring):

British actress Minnie Driver starred as Lorraine Finster, the mistress of Stan Walker (Karen’s husband). She appeared in a number of episodes and continually butted heads with Karen. Lorraine was also briefly Karen’s step-daughter, when Karen married Lorraine’s father Lyle, played by John Cleese.

Elton John as himself (Appearance: S5, E10):

Worldwide superstar Elton John briefly appeared as himself in a season five episode of W&G. During the episode, Jack tried to convince Will that the gay mafia exists, but Will doesn’t believe him. Elton overheard Will talking about it at a restaurant and promptly introduced himself as THE gay mafia!

Michael Douglas as Detective Gavin Hatch (Appearance: S4, E23):

When Will’s laptop is stolen, Michael Douglas is the detective who handles his case. But when Gavin develops an interest in Will, he creates an elaborate ruse which sees the pair go to a gay nightclub in order to stake out the person responsible for stealing the laptop.

Molly Shannon as Val Bassett (Appearance: reoccurring):

Molly Shannon played Will and Grace’s kooky neighbour Val, who appeared in several episodes and created havoc for Grace. Not only did Val become obsessed with Jack for a time, but she also went so far as to steal Grace’s sketches as pass them off as her own designs!

Sharon Stone as Dr Georgia Keller (Appearance: S7, E20):

Blonde bombshell Sharon Stone starred in one episode of W&G in 2005 when she played Will’s therapist Georgia Keller. But things got messy when Will suggested that Grace go and see her too. The pair hit it off instantly and Will is left feeling jealous when Georgia asks Grace to be featured in her upcoming psychology book.

Madonna as Liz (Appearance: S5, E21):

After her divorce from Stan is finalised, Karen decides that she wants to connect with “real people” more, so she decides to answer a roommate wanted ad. Madonna stars as Liz, Karen’s new roommate who turns out to be a totally bizarre office worker who is very particular about her house. Things turn sour between then when they end up fighting over the same guy. Karen then reveals that she in fact owns the WHOLE apartment building and Liz better look for alternative accommodation!

Harry Connick Jr as Leo Markus (Appearance: reoccurring):

Crooner Harry Connick Jr landed a reoccurring role on Will & Grace as Grace’s husband Leo. The pair met when Grace was on her way to the sperm bank to be implanted with Will’s sperm in order to try for a baby. Meeting the handsome stranger threw Grace off her course and the two ended up getting married. At the end of the original series the couple end up together, married with a baby girl, but where will Leo be in the new reboot?

Taye Diggs as James Hanson (Appearance: reoccurring):

American actor Taye Diggs, known for his roles in Empire and Private Practice, appeared in four episodes of Will & Grace. He starred as Will’s love interest James, who was first introduced when the pair ran into each other at a movie theatre and felt an instant connection. Will and James ran into each other again during a trip to LA and Grace offered to marry James, who was in the process of being deported back to Canada, in order for Will to get to know him. After the wedding, Will discovers that James is quite self-centred and asks Grace to get the marriage annulled.

Cher as herself (Appearance: S3, E7):

In what is possibly the best cameo of all time, Cher made an appearance in season three of Will & Grace when she approached Jack in a restaurant. Jack was a huge fan of Cher, even carrying around a Cher doll with him, but he was unconvinced that Cher was in fact Cher. Jack calls Cher a drag queen and tells her to work on her Cher impersonation.

Debbie Reynolds as Bobbi Adler (Appearance: reoccurring):

Vivacious movie star Debbie Reynolds regularly appeared in the original series as Bobbi Adler, Grace’s outspoken mother. Bobbi and Grace had a somewhat strained relationship at times as Grace thought she could never live up to her mother’s expectations. Debra Messing has confirmed that a tribute to the late Debbie Reynolds will be featured in the reboot of Will & Grace this year.

Britney Spears as Amber-Louise (Appearance: S8, E18):

Pop star Britney Spears made a cameo on W&G in the final season and starred as Jack’s new co-host of his talk show Jack Talk. When OutTV, the network that broadcast Jack’s show, were purchased by ultra-conservatives, they introduced a co-host in the form of Amber-Louise, who posed as a conservative Christian, but was anything but.

Jennifer Lopez as herself (Appearance: S6, E23 & E24; S7, E1):

Singer and actress Jennifer Lopez starred in three episodes of W&G, each time appearing as herself. Jennifer first appeared when Karen asked her to perform at her and Lyle’s wedding reception, but Karen ends up stopping the wedding.

Janet Jackson as herself (Appearance: S7, E2):

Following Jack’s brief run as Jennifer Lopez’s backup dancer, Jennifer recommended Jack to Janet Jackson and set up an audition for him. Unfortunately Jack is forced to have a “dance off” against another dancer called Artemus (Will Arnett) to win a position in Janet’s squad. Ultimately Jack and Artemus are both fired when things turn personal between them when Karen reveals that her and Artemus were former lovers.