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Machine Gun Kelly

Started out doing rap and in general his rap music wasn't particularly well liked. The dude also infamously released a diss track aimed at Eminem which backfired big time, with Em releasing a counter diss track which many agreed was the superior song. In the past couple of years MGK switched from rap to pop-punk rock music heavily influenced by late 90s and early 00s acts like Blink 182 and early 00s Green Day and the general reception to his music has greatly improved, with the dude now earning a decent amount of praise and hell he even got one of his songs in the recent Tony Hawk's Pro Skater 1+2 remake.

Poppy

The stage persona of singer Moriah Rose Pereira, Poppy was always a subversive act, but her early stuff stuck close to her namesake by being very "poppy" music. Still decent pop music, but starting with her second album "Am I a Girl?" she began to also show influences from industrial metal (especially noticeable with her collab with Grimes on "Play Destroy"). This would be taken further with her third album "I Disagree" which is far more influenced by the likes of industrial and nu metal, and it's even speculated that the uncredited feature on the song "Fill the Crown" is likely Marilyn Manson, who is in fact a fan of hers. It was also around the time of the third album's making that Poppy finally split from her emotionally abusive ex-manager (and possibly ex-boyfriend) Titanic Sinclair, signed with Sumerian Record, a label that mainly signs djent metal bands, and started a relationship with horrorcore rapper Ghostemane, so it's likely the split from Titanic means she's showing more of her true self in her recent music.

I'd say Bring Me The Horizon. They went from metalcore to hard rock to pop and probably back to hard rock again but with a pop twist. Their move to pop made them more well known outside of the UK and Oli Sykes is a pretty good singer.

Not sure if this counts since his abstract style hasn't changed so much, but Kenshi Yonezu, formerly known as Hachi. He started out as vocaloid producer, but retired from the medium and began to cover his songs himself. As far as retired vocaloid producers go, he's achieved considerable mainstream success and popularity in Japan on his own. His late compatriot, Wowaka, I feel wasn't equally as successful from distancing himself from his past legacy. Not to say he didn't have his limelight with his band, Hitoire. But his death cemented his vocaloid stardom even moreso and is what people will mostly remember him for.

When The Cure went from, uh… whatever the fuck their first album's genre was meant to be to the darker, goth genre for Seventeens Seconds, Faith and finally Pornography. Those three albums are still their best works after all these years.

The least obscure answer one could give, but the Beatles. I'm personally not a big Beatlehead, and this may be coming from a place of ignorance, but their earlier music sounds like generic pop/rock of the time which I don't care for. While they stayed under the rock genre umbrella, their later experimental/prog phase is when they made most of their songs that I like.

Bathory went from generic black metal to viking metal, which I vastly prefer

Trophy Scars started out as just post-hardcore but as time went incorporated blues into their music, making it way more interesting

their latest album imo is their masterpiece

Swans originally started as a no-wave and industrial rock band in New York before the genre movement died out. Their style evolved into gothic rock and later into post-rock would not only become their defining style of music but arguably come to perfect within their reformation in 2010 with a string of albums that would arguably define their legacy as one of the greatest experimental rock outfits.

>My Father Will Guide Me up a Rope to the Sky
>The Seer
>To Be Kind
>The Glowing Man

Outside of My Father Will Guide Me up a Rope…, a good album on its own merits, the albums of The Seer, To Be Kind, and The Glowing Man (known among some within the Swans fanbase as "the trilogy") would not only revitalize the band but establish them as legendary among experimental rock, as these 3 albums would garner critical acclaim among critics.

They also happen to be incredible albums in my mind, with To Be Kind being my personal favorite and one of my favorite albums of all time.

I don't know if it's more of a change in genre as much as it is an evolution of a band, but I think it fits here.

The Beach Boys

They started out as a rather generic pop group, but when Brian Wilson took creative control they managed to go into baroque/psychedelic pop and make some of my favorite music ever