[2][5] Once in high school, the pair began organizing and promoting parties which "leaned heavily on a mix of Southern and Midwestern rap".

[6] The pair also promoted artists from Florida's burgeoning SoundCloud rap scene under the brand name Dope Entertainment before noticing the need for a genre-specific music festival.

[7][8] The first Rolling Loud took place in Miami, Florida in February 2015 and featured artists such as Schoolboy Q, Juicy J, Currensy, and Action Bronson in the one-day event.

[7] In 2016, Rolling Loud was held at the larger Mana Wynwood convention center and featured Ty Dolla $ign, Young Thug, and Future as the headlining acts.

[59][60] In 2018, at Rolling Loud in Miami, Meek Mill made his second live performance after being released from prison with a surprise set at the festival.

[62] In 2018, Young Dolph flew out Duke University Baristas who were fired for playing his music and gifted them $20,000 on stage at Rolling Loud Miami.

[66] In 2019, at Rolling Loud in Los Angeles, a 23-year-old attendee named Kalvin Sanchez was assaulted and rushed to the hospital after suffering serious head injuries.

The lawsuit claimed that Scott was being negligent by encouraging the crowd to become more aggressive while people were "being injured, suffocating, losing consciousness, fighting and being trampled".

[71] In response, Cudi gave the crowd an ultimatum to curtail its unruly behavior, but after another object was thrown at him, he cut off his performance and left the stage.

[75] In 2023, Don Toliver brought out surprise guests Kali Uchis, James Blake, and Justin Bieber during his set at Rolling Loud California.

[78] On December 9, 2022, Rolling Loud released its first single titled "Finger Food" featuring Rae Sremmurd and Duke Deuce.

[80] In 2021, rapper Zoey Dollaz and Rolling Loud Co-Founder, Tariq Cherif, chartered several jets to Haiti to provide supplies to people in the wake of a massive earthquake.

[81] In 2022, The Miami Jr. HEAT teamed up with Rolling Loud to host 50 local children from After-School All-Stars for a basketball clinic at the festival.

[86][87][88] In 2024, Rolling Loud won the Silver ANA SeeHer REGGIE GEM Award for their Forever 21 x Bunny's Bae Bar collaboration.