I would start:


First Album: 2004
Second Album: 2024
a 20 year gap.
She also has a song released in 2013 in her 2024 album.

We know how it went for her.
she tried to debut/be a singer in 2004 and then became a full time writer and then TRIED to become a singer again post 2013
but her career has been SO messy!

Post more artist you know.

SZA switching from being a marine biologist to a singer

I mean, Lily Allen comes to mind. Only because she's tried so hard to veer away from what she's best at: Music. 

 

She released two albums before she was over it, went off and got married, had kids.

Opened up a short-lived vintage boutique with her sister.

Released her first "comeback" album, Sheezus, 5 years later.

Took another long break.

Released her next album, No Shame, 4 years later, after getting divorced.

Got remarried. Started doing Broadway-equivalent plays. Did a podcast.

Got divorced again, then randomly dropped her magnum opus, West End Girl, at 40 years old.

No pre-release campaign, no singles, critically acclaimed, still having streaming increases a week after release...

 

Really unique situation to be in. I'm hoping this all serves as a reminder to her how strong her pen is. 

Erykah Badu is also a Doula. she has delivered babies for Summer Walker and many others! I dont consider it weird, but definitely unique and honorable. 

Ava Max. From popstar to dental assistant to realtor. 

Sia's career is interesting to me. She was more indie in the 2000s and as she started writing for more artists in the 2010s, she became mainstream, defying  age barriers.

I love Katy but I think her career is weird. She break many records with Teenage Dream. Yet after that everything went downhill. And of course it's nothing new seeing popstar flopping but that much? From that power? A lot of her decisions are looking like she was sabotaging herself 

Katy going from Christian Rock (as Katy Hudson) to horny dance pop 

 

 

 

 

 

Edited October 31, 2025Oct 31 by Lethal

My girl Tori Kelly

 

29 minutes ago, HASHTAGPOW said:

Ava Max. From popstar to dental assistant to realtor. 

she's uber driver now

 

Grimes. 

 

She went from living on a boat with her chickens to being a critically acclaimed musician known worldwide, to being married & having kids with one of the world's richest men to fighting for their custody while warning everybody about the dangers of AI since a decade ago, only to be misunderstood & reduced to a controversial internet celebrity. 

Vitamin C.

 

Studied in NYU

Joined a rock band

Acted in movies

Has a Pokemon movie track

Released pop music

Was in a front cover with Beyonce and P!nk

Became an executive at Nickelodeon

Helped Tinashe launch her career

Now is a music executive at Netflix

Songwriters like Bonnie and Sia will always have weird careers. Skylar Grey also comes to mind when it comes to it.

- Her first charting song ended up at #4 as she did the hook for a Mike Shinoda song in 2005, back when she didn't have the 'Skylar Grey' name yet

- Released a flop album in 2006 under her real name

- Became Eminem's heir, writing hooks for his songs, and getting Love The Way You Lie with it (and a song with Diddy )

- After so much delays and buzz singles, she finally released her second album in 2013, which was frontloaded, but she got her only top 10 album from it

- Despite her solo music flopping, her career as a songwriter was thriving, and even got a few more hit collabs with David Guetta and Macklemore (and even Nicki Minaj, depending if you count Bed Of Lies as a minor hit)

- Her third album, and last major label album was released in 2016. The collab with Eminem was kinda a potential hit, but the lyric content and the scrapped music video were too violent, it was her last chance to make it in the mainstream as a solo artist, but seems like it wasn't meant for her

- Kept releasing versions of the songs she wrote, buzz songs, cover, movie soundtracks, and Emimem songs. She became the 'first woman to produce an Eminem song', which doesn't speak well of Eminem, but I guess it does for Skylar 

- Self-released an album, went through personal problems, her divorce ended up being too messy so she ended up selling all of her music rights in order to get out of that marriage 

- Self-released last week another album that was already an EP years befofe, so yeah, too much of a mess...

33 minutes ago, youngpopariana said:

My girl Tori Kelly

 

To be fair, she went as far as a Youtuber/Viner-turned-into-popstar could get 

Samantha Mumba came to mind when I read the OP. Irish singer, signed when was about 16, debut single at 17 in 2000 ("Gotta Tell You") which was a huge hit reaching #1 in Ireland and top 5 in the UK and the U.S. which is a huge achievement for an international act, another #1 Irish single in 2001, and an album which did okay. Then released a single which was planned to be the first off her second album and it did pretty well (top 5 in the UK and Ireland) but the album was shelved and she didn't release another single till 2008. Her and her label basically stopped - she began acting a bit and so did her younger brother. It seems it was an amicable decision between her and the label but I'm not sure.

 

Since 2008 she's released a handful of singles. She has resurfaced in the music business sometimes over the years - notably this year when she released a song that was a contender for the Irish Eurovision entry but it was beaten in the public vote. She performs now and then nowadays too.

 

I find it wild that she had a debut album campaign that was really successful in the States and then just dipped after one more single 

Edited October 31, 2025Oct 31 by holyground13

Mike Posner.

Christina Aguilera.

 

Popstar -> featuring singer -> Indie Spanish singer -> Selling cookies -> Selling lube. 

Sky Ferreira 

I love weird careers and weird career trajectories.

Mariah Carey - She owned the entire '90s and most of the 2000s with hit after hit only to be known exclusively as "The Christmas Lady" now. 

 

Taylor Swift - Starting out as a sweet country girl only to transition to pop (it's very rare for an artist to successfully do that), becoming arguably the hugest female pop star of all time off the most bland, inoffensive background music.

 

Justin Bieber - Most child singers outgrow their "cute" phase and quickly fade away. You never hear their songs anywhere besides the Disney Channel, Nickelodeon, etc. Their teen girl fans grow up, outgrow them, and then you never hear their names again. It is very unusual for someone like him to still be so popular well into his adulthood. 

 

Lady Gaga, going from performing in bars and clubs, to becoming a popstar, then a jazz artist, then starting a makeup brand, then trying a film career, then entering the pharmaceutical industry, partnering with Nurtec to advertise pain medication. What a ride

Edited October 31, 2025Oct 31 by Icarus

Sabrina Carpenter,  Cardi B and Lil Nas X

 

One randomly became a huge star after 6 flop albums and in a very short time span the other one went from being a stripper to one of the biggest rappers of all time. Lil Nas X was also an unlikely superstar, coming out as gay at the peak of his career and smashing worldwide with gay bops back to back.

 

Bonus : Akon randomly deciding to start making music in his 30s and becoming one of the biggest stars of the 2000s. 13 year old Bhad Bhabie going from being a hot mess  on Dr Phil to being a household name by the next year with  a lucrative rap career to making $50 million on Only Fans by age 18. Random Australian woman Iggy Azalaea  becoming the first white female rapper to smash in America/WW, getting a #1 hit before Nicki Minaj could. Lana Del Rey only having one top 10 hit but always smashing on streaming, dozens of streaming hits with over 500 million streams despite  not having a commercial sound and barely charting . Multiple songs that were not pushed as singles/ not played on radio  but have a billion in streams .i.e Cinnamon Girl, Say Yes To Heaven...