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CupcakKe would upload her first video to YouTube since her previous deletion of all videos on her channel in 2019 with the double video for previous singles "Grilling Niggas" and "Lawd Jesus", released on May 13, 2020.

On January 11, 2019, the single Squidward Nose was released, and on February 21, 2019, a music video for the song featuring John Early premiered. On April 17, 2019, Harris released a remix of Lil Nas X's song "Old Town Road" titled "Old Town Hoe". It was released exclusively on her YouTube channel. On May 10, 2019, Cupcakke posted an update to Twitter and Instagram with the caption "Old Town Hoe Video is almost finish". The video was released the following day.

In September 2019, Harris announced her retirement in an Instagram live video, stating, "This live is going to be the last video that y'all [will] see of me". She stated that she would no longer be releasing music to the public and that she would be removing her music from all streaming platforms. In the same livestream, Harris announced that she would be cancelling her The 10k Giveaway Tour, as she tearfully explained that she was "corrupting the youth" with her raunchy songs. She stated that she was disturbed to see children in videos and young people at her shows singing along to her explicit songs, and said "I want to go to heaven after this. I don’t want to go to hell”. Harris also told fans that she has a "very bad gambling addiction" and that she had lost $700,000 at a casino in September 2018. She concluded the video by thanking her fans for their support and for saving her and her family from homelessness which they experienced prior to Harris' career in music.

Concerned fans suspected that her "social media meltdown" may have been a result of her recent struggles with mental health, following a series of worrying posts on social media. On January 8, 2019, Harris was reportedly taken to a hospital in Chicago after tweeting that she was going to commit suicide. In a tweet posted the next day, Harris wrote "I've been fighting with depression for the longest. Sorry that I did it public last night but I'm ok. I went to the hospital & I'm finally getting the help that I need to get through, be happy, & deliver great music. Thanks for all the prayers but please don't worry bout me."

On November 7, 2019, CupcakKe came out of retirement after a 40-day absence on all social media platforms with a tweet; "Jesus fasted for 40 days & so did I...... Nov 16th". On December 29, 2019, CupcakKe announced that she had signed an $8 million record deal. On March 6, 2020, CupcakKe released a new single, "Lawd Jesus."

Her second mixtape, S.T.D (Shelters to Deltas), was released in 2016 and was included in Rolling Stone' s June 2016 list of the "Best Rap Albums of 2016 So Far". She has also received attention from music publications Complex and The Fader. Following the release of her mixtapes, Cupcakke debuted her album Audacious in 2016. Her second studio album Queen Elizabitch was released in 2017. In 2018, it was followed by her third studio album Ephorize. Later in 2018, Cupcakke released Eden on November 9, 2018.

On January 15, 2018, Harris posted the music video for her song "Duck Duck Goose", from Ephorize, on YouTube which garnered attention from music publication sites such as Vice and Genius. The Fader wrote about it, stating that the "visual features the Chicago rapper showing off an extensive collection of dildos as well as a souvenir Statue of Liberty. " On February 20, the music video for "Fullest", another track from Ephorize, was released which drew more attention with Out calling it "a house party for the Instagram generation... Millennial pink palette: check. Inflatable pool animal: check. Neon backlighting to ensure everyone finds their best angle: check." The video was also recognized by international publications such as Konbini and Ismorbo.

On November 9, 2018, Harris released her fourth studio album, Eden. The music video for "Quiz", the lead single, was released on YouTube on May 21, 2018. The music video for "Hot Pockets" was released on July 5, 2018. The music video for her third single, "Blackjack", was released on August 15, 2018.

Cupcakke is often noted for her hyper-sexualized, brazen, and often comical persona and music. Since her debut, she has developed a strong online fanbase, whom she nicknamed "slurpers". Cupcakke has also used her songs as a platform to advocate for LGBT rights and encourage female empowerment. In a 2017 Interview, Cupcakke stated "Anything guys can do, girls can, and most of the time, they're out there working harder and doing it better".

In February 2017, Harris released "Cumshot", which served as the lead single to her second studio album. On March 7, English singer-songwriter Charli XCX premiered her song "Lipgloss", which featured Harris. The song was later included on XCX's mixtape, Number 1 Angel, which was released on March 10.

On March 24, 2017, Harris officially announced her second studio album, titled Queen Elizabitch, which was released on March 31, 2017. The Fader described it as "the type of nasty rap that made her a viral sensation, alongside all-out pop bangers like "33rd" and the confessional a cappella freestyle "Reality, Pt. 4." Stereogum also noted that the album "sees CupcakKe engaging with the current political climate and radio trends in a way that could help her cross over to a more mainstream audience".

On April 7, 2017, Queen Elizabitch was removed from online streaming services and digital music stores due to an illegal backing track that Harris had purchased from what she described as a "shady producer". She soon announced on Twitter that Queen Elizabitch would be re-released on April 16, 2017.

On September 1, 2017, Harris revealed a new single, "Exit", and its release date on her Instagram account. It became available for digital download on September 15, 2017. On November 6, 2017, Harris announced on her Twitter the release of her new single, "Cartoons". It was released November 10, 2017.

On December 20, 2017, Harris announced through Twitter that her third studio album, Ephorize, would be released on January 5, 2018. Exclaim! called it "her most polished work to date" and noted that "she still slides in plenty of deliciously dirty one-liners throughout the new record." HotNewHipHop commented that "Ephorize might be one of the most introspective bodies of work she's dropped off to date." Pitchfork awarded the album with the publication's "Best New Music" accolade, calling it Cupcakke's "best album yet, with terrific production and a barrage of raps that reveal Elizabeth Harris to be far more than her hilarious and absurdly raunchy one-liners."

In June 2016, Harris released her second mixtape, S.T.D (Shelters to Deltas) It was preceded by the single "Best Dick Sucker". Other tracks, such as "Doggy Style" and "Motherlands", were also later released as singles. The mixtape was listed among Rolling Stone's "Best Rap Albums of 2016 So Far".

In October 2016, Harris released her debut studio album, Audacious. The album was preceded by the single "Picking Cotton", which was described by MTV News as "a protest song about racist cops". Other tracks on the album such as "Spider-Man Dick" and "LGBT" were accompanied by music videos. In an interview Harris stated that she made the song "LGBT" "...strictly for the gay community to know that they are loved and don’t need to feel judged."

In October 2015, the official music video for her song "Vagina" was released on YouTube via YMCFilmz. According to Cupcakke, she wrote the song because she was inspired by Khia's song "My Neck, My Back". One month later, Harris released "Deepthroat" on her own channel. Within weeks, the two videos went viral on YouTube, Worldstar, and Facebook due to their overt sexual nature and raunchiness. The songs later became singles for Harris' debut mixtape, Cum Cake, which was released in February 2016. Its release was also supported by further singles such as "Juicy Coochie", "Tit for Tat", and "Pedophile". A writer for Pitchfork called the mixtape a "well rounded introduction to a skilled writer" and said it used songs "about love, loss, and hardship with its more explicit tracks to create a full profile of the up-and-coming Chicago rapper". "Pedophile" was also specifically noted for its powerful lyrics and blunt commentary on sexual assault.

Harris released her first music video, "Gold Digger" onto her official YouTube channel in August 2012, which went viral on the internet. She was only 15 at the time of its release—the original video has since been deleted. Over the next few years, she continued to release original music, as well as freestyles using beats from other artists, through her YouTube channel, where she has amassed over 500,000 subscribers.

Elizabeth Eden Harris (born May 31, 1997), known professionally as Cupcakke (often stylized as cupcakKe), is an American rapper, singer and songwriter from Chicago, Illinois. Cupcakke began her career as a rapper by releasing material online in late 2012. In 2015, two of her songs, "Deepthroat" and "Vagina", went viral on video-sharing websites such as YouTube and WorldStarHipHop. The songs were later included on her debut mixtape, Cum Cake (2016), which was placed at number 23 on Rolling Stone' s "Best Rap Albums of 2016" list.

Harris was born on May 31, 1997, in Chicago, Illinois, and was raised on King Drive, near Parkway Gardens. Harris was raised by a single mother and spent nearly four years in Chicago's homeless shelters starting at age seven. She grew up and went to school with other established Chicago rappers such as Lil Reese and Chief Keef. She got an early start into music and poetry at the age of 10 by her involvement in her local church. It was also there that she got her start in performing, where she would perform for her local pastors by reciting poetry about her Christianity and faith.