Social media was set afire with the news that Sex and the City will be returning for a revival on HBO Max. The acclaimed series, which went off the air in 2004, is widely credited for being incredibly groundbreaking in the way that it dealt with women’s issues — and to this day, legions of devoted fans turn to the exploits of Carrie Bradshaw and her friends for escapist entertainment.

Sex and the City might have featured four main stars in the leading roles. But, over the years, the series welcomed a whole host of talented guest stars, including Matthew McConaughey — who was at the time one of Hollywood’s hottest up and coming leading men. 

‘Sex and the City’ is an iconic TV show

Sex and the City debuted on HBO in 1998. Starring Sarah Jessica Parker as Carrie Bradshaw, a New York-based writer looking for love in the big city, the series also starred Kim Cattrall as Samantha Jones, Kristin Davis as Charlotte York, and Cynthia Nixon as Miranda Hobbes, Carrie’s best friends.

The four women all experience their fair share of problems in love, but they always have each other to turn to, even in their darkest moments.

Through it all, Carrie’s romance with Mr. Big, played by Chris Noth, is a central storyline. Carrie and Big go through years of on-again-off-again romance before they finally find their happily-ever-after. While the series ended on a bit of a cliffhanger for Carrie and Big, the story was continued in two major feature films: Sex and the City, released in 2008, and Sex and the City 2, released in 2010. 

There were many major guest stars on ‘Sex and the City’

Over the years, especially as Sex and the City became more and more popular, celebrity guest stars began appearing on the show. While some of these celebs appeared only in small cameo roles (such as Heather Graham) others were featured in fully-developed storylines, including an episode where David Duchovny played one of Carrie Bradshaw’s boyfriends.

A few of the other stars who played guest roles in Sex and the City include Kat Dennings, Jon Bon Jovi, Bradley Cooper, and Sarah Michelle Gellar.

Still, one of the most popular celebrity guest spots was played by McConaughey, well before he started getting nominated for major awards. McConaughey’s role in a season three episode of Sex and the City is one that really resonated with fans — even though, as it turns out, the role wasn’t even originally written for him. 

How did Matthew McConaughey land his guest spot on ‘Sex and the City’?

In the series, McConaughey played a fictionalized version of himself. According to Marie Claire, McConaughey wasn’t the first actor to have been offered the role of the charismatic and intense Hollywood power player who envisions himself playing Mr. Big in the Sex and the City movie. In fact, he was the fourth to have been offered the role.

Marie Claire describes how the first actor who was courted for the part was Alec Baldwin, who turned it down. Showrunners then offered it to George Clooney, who turned it down. Then, famed actor Warren Beatty was offered the part — he also turned it down.

Finally, showrunners offered the role to McConaughey, who accepted it. For many Sex and the City fans, McConaughey is the only actor that they can envision in the role — even if he was far from the first to be offered the part.

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