Will & Grace has definitely proved itself to be one of the craziest shows on television. Over the years, the zany characters have done tons of insane, yet hilarious things. Here’s a countdown of seven of the craziest moments from the past nine seasons.

1. Cher’s cameo

Episode 7, Season 3

What could be crazier than one of the biggest superstars of all time guesting on an episode? When Cher appeared, playing herself, the laughs were aplenty when Jack is convinced she’s a drag queen and proceeds to do his Cher impression for her.

2. Will comes out to Grace

Episode 8, Season 3

This flashback episode harkens back to the 80s when Will and Grace were actually engaged to be married! When Will realizes he needs to break the news to Grace about being gay, a totally awkward conversation takes place between the two.

3. Karen pretends to be a maid

Episode 18, Season 5

Karen does all sorts of crazy things on the show, but one of the most unexpected events took place when Karen pretended to be a maid just to gain the affections of a maintenance man. Seeing Karen in a maid’s uniform is outlandish enough, but then Karen earns even more laughs when she tries dusting with the stick end of the feather duster!

4. Will and Jack wake up in the same bed

Episode 1, Season 6

Will and Jack imbibe a little too much on an overnight cruise and are shocked to wake up in the same bed the next morning. As they try to piece together what happened the night before, both are hilariously stunned to have been possible bedmates.

5. Will and Karen make cleavage adjustments

Episode 8, Season 7

Grace always relies on her friends for dating advice, and when she’s getting ready for a new date, Will and Karen are more than obliged to make some cleavage adjustments to help her look her best. Laughs ensue when both of them try to drag out the scene as much as possible.

6. Jack uses anti-aging magnets

Episode 2, Season 9

Jack’s vanity makes him willing to try anything to look younger. Karen suggests tons of anti-aging techniques, including magnets that pull the skin back. Unfortunately, Jack experiences a magnet mishap and ends up getting stuck to everything in sight.

7. The show imagines an old-fashioned Christmas

Episode 7, Season 9

Nothing could be crazier than imagining our favorite foursome experiencing Christmas back in the early 20th century. With Jack’s portrayal of a gay sailor and Karen’s role as a poor mother of a bunch of children, fans were treated to a wacky Christmas story that’s destined to be a classic.

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