Celebs Who Tried To Massively Overhaul Their Image

Ashley Hunte
The lens of a camera, ready to snap a shot.
Unsplash | ShareGrid

Like everyday folk, celebrities have multiple interests, and like to shake their careers up every now and then. It might not always work out, but they still get points for effort.

Or, it could work out wonderfully in their favor. I guess it just proves that you won't know until you try.

For better or for worse, here are some celebrities who took a shot at reinventing their careers.

Taylor Momsen.

Maybe you remember her as Cindy Lou Who in 2000's How the Grinch Stole Christmas, or maybe you remember her as Jenny Humphrey in Gossip Girl. But Momsen's career took a pretty unexpected turn while she was still acting on the teen drama.

She, in fact, started a rock band.

Known as the Pretty Reckless, Momsen and her band have gone on to release four studio albums, and tour with the likes of Evanescence and Fall Out Boy. Momsen retired from acting and left Gossip Girl, but she returned for the show's finale.

Paris Hilton.

One of the 2000's most iconic fashionistas, socialites, and reality stars, there are actually very few things Hilton hasn't tried. Her foray into acting was definitely one of her most notable attempts to change her image, and it definitely didn't go well.

She's also tried singing, which didn't stick either.

But in more recent years, Hilton tried her hand at DJing, and nowadays runs a podcast called This is Paris. It seems like the star has finally found her footing.

Lady Gaga.

Gaga's done what many singers have tried, and few have been able to do successfully: she transitioned from music to acting. And considering the acclaim she got for both American Horror Story and A Star is Born, it's safe to say she did it pretty well.

Of course, she hasn't left her singing career behind.

She's currently on tour promoting her 2020 album, "Chromatica." In addition to all that, she recently launched a cosmetic line, Haus Labs. Gaga's definitely keeping herself busy nowadays.

Dwayne Johnson.

The Rock in his wrestling career taking off his sunglasses and raising one eyebrow

Known as "The Rock" during his professional wrestling career, Johnson has made a slow, ultra successful transition into acting. He's starred in a bunch of well-received films, like Moana, as well as several films in the Fast and the Furious franchise.

And he's showing no sign of slowing down.

He has a show based off his own life, called Young Rock, which has been airing since 2021. He's also set to make his superhero (or antihero) debut in the upcoming film, Black Adam.

Shaquille O'Neal.

Shaq was a huge name in basketball during his time on the court, and continues to be talked about with legend status to this day. But his ventures off the court have been... interesting. And there have been a lot of ventures.

Like others in this list, Shaq has tried his hand at acting.

Shaquille O'Neal as Kazaam with a towel magically cleaning his ears

Remember Kazaam? Yeah, like that film, his other attempts at acting didn't quite pan out. Though, he does still appear in shows and movies from time to time.

Interestingly, he also released a rap album in the '90s. And he's published a number of children's books.

Jane Fonda.

Jane Fonda's had a successful acting career that's spanned decades, with her first appearance being in the play, There Was a Little Girl in 1960. She was nominated for a Tony for that role.

In the '80s, she began recording and releasing exercise videos.

The tapes ended up being super successful. After retiring from acting altogether in the '90s, she returned to the screen in the 2000s, and has appeared in a number of shows since.

Taylor Swift.

As Swifites are sure to remember, Taylor started out as a teen country darling before transitioning into a true pop sound. And more recently, with 2020's "Folklore" and "Evermore," she's transformed her sound yet again (and everyone loves it).

Though, not all of her career transitions have been successful.

Taylor Swift in the 2019 Cats movie.
Giphy | Cats Movie

For instance, Swift has tried her hand at acting more than once, and none of her films really gave her much acclaim (especially not 2019's Cats, which was kind of rough on the whole cast).


Aubrey Graham intro scene from 'Degrassi'
Giphy | Complex

If you're of a certain generation (and Canadian, most likely), you'd probably remember Aubrey Graham as Jimmy in Degrassi: The Next Generation. He was actually on the show for a long time, between the years 2001 and 2008, before leaving to pursue rap.

And he's definitely found success as a musical artist.

He's released a number of critically acclaimed albums, including 2022's Honestly, Nevermind. And over the years, he's been incredibly influential to hip hop, and pop culture in general. Let's not forget that he's the one who popularized "YOLO."

Bo Burnham.

Bo Burnham started out like a lot of young people in the mid and late 2000s: he had a YouTube channel. He mostly did comedy skits and played funny songs, and had a great deal of success on the platform.

He then got into making comedy specials.

Bo Burnham laughing and clapping at an awards show.
Giphy | Film Independent Spirit Awards

Now, Burnham is known as a comedian in his own right, with several Netflix specials under his belt. He's also found success in filmmaking, having written and directed Eighth Grade, and had a role in 2020's Promising Young Woman.

Jordan Peele.

A 'Key and Peele' sketch in which a doorman played by Key reels in another doorman played by Peele, who says "The Oscar goes to..."
Giphy | Comedy Central

Peele was a comedian, working on Mad TV in the 2000s. Then, he continued comedy acting alongside Mad TV castmate, Keegan-Michael Key, in their own show called Key and Peele. And then, he decided to get into directing horror and thriller films.

It seems like a huge jump to go from comedy to horror, but he made it work.

Jordan Peele at an awards ceremony in a white tux
Giphy | The Academy Awards

2017's Get Out completely revitalized the comedian's career, earning him the Oscar for Best Original Screenplay. He's gone on to write, direct, and produce a number of other films, including 2021's Candyman and 2022's Nope.