2016–2019: Beneath the Willow Tree and other singles KennyHoopla began posting songs to his SoundCloud page in 2016. On October 5, 2016, he released an EP titled
Beneath the Willow Tree to SoundCloud, which consisted of some of the tracks he had posted throughout the year, as well as some new songs. The EP received acclaim from several music blogs, who considered him an artist to watch. On October 26, he uploaded the song "Cave" to SoundCloud, which became his most streamed song on the site at the time. On August 6, 2017, he released his commercial debut single "Waves", along with a music video. This was followed by "Sickness" in 2018. In 2018, he signed with Arista Records. On February 1, 2019, he released the single "Lost Cause", which became his most popular song at the time and gained him more exposure. Its music video was released on February 6. This was followed by "Sore Loser" on September 18, which was also positively received.
2020–present: ''How Will I Rest in Peace if I'm Buried by a Highway? and Survivors Guilt: The Mixtape'' On February 4, 2020, KennyHoopla released the single "How Will I Rest in Peace if I'm Buried by a Highway?" This track quickly became his most popular song to date, becoming his first song to reach 1 million views on YouTube, and garnering praise for its unique
post-punk and
new wave inspired sound. The track also received radio play on alternative music stations, and peaked at number 8 on the
Billboard Alternative Airplay chart. On March 12, he released the follow-up single, "The World is Flat and This is the Edge". On May 13, 2020, he released the single "Plastic Door", and announced that his EP ''How Will I Rest in Peace if I'm Buried by a Highway?'' would be released that Friday, May 15. The EP received critical acclaim, being praised for its versatile mixture of sounds such as
indie rock,
hip hop,
pop punk, and
drum and bass. On October 14, he released another version of the song, this time featuring guest vocals from
Jesse Rutherford of
The Neighbourhood. On October 12, 2020, he revealed that he is working on his debut album. Two days later, on October 14, he posted a picture to his Twitter account of him in the studio with
Blink-182 drummer
Travis Barker. On November 20, he released the song "Estella", which features Barker on drums. Its music video was released five days later, on November 25. On May 7, 2021, he released the single "Hollywood Sucks" featuring Travis Barker, and announced the release of his mixtape
Survivors Guilt: The Mixtape on June 11. KennyHoopla is scheduled to support
Yungblud in London on his Occupy the UK tour in 2021, and
Machine Gun Kelly on his 2021
Tickets to My Downfall U.S. tour, alongside
Jxdn and
Carolesdaughter. In 2022 he released the rap-influenced single "DIRTY WHITE VANS". He released further singles throughout 2023 before parting ways with Arista Records. He independently released the single "ONE TULIP" in summer 2024. On May 30 2025, he released the three-song EP
rebirth // renaissance, followed by EP C
onditions of an Orphan on September 19, 2025. The EP was produced by Paramore’s Zac Farro. In an interview with
The Luna Collective, La’ron described the release as “getting up to get back in the fight” after getting knocked down by the music industry. The title references the loss of his mother and lack of mentors in his life at the moment. KennyHoopla opened for Soft Play on tour in September 2025, and embarked on a 9 date headline tour of the U.S. in November. In October 2025, KennyHoopla announced a UK and Ireland headline tour in support of
Conditions of an Orphan. The tour will include dates in Glasgow, Manchester, London, and Bristol, with support from the band girlfriends. ==Musical style==