Prior to its release, Simco entered a US$4 million joint partnership with Stampede Management and BMG for his Neon Nation label and production company.

Simco was formerly a member of the hip hop group Three Loco, along with Andy Milonakis and Dirt Nasty, who reunited on his Balloween 2016 Halloween mixtape performing "Bitches in my Driveway".

[14] Riff Raff took advantage of social media on Myspace, YouTube and WorldStarHipHop in late 2008, releasing songs, freestyle-videos, and sketch clips, which showcased his talent as slapstick and performance art.

Like many other artists from Houston, Riff Raff also spent much of his time selling CDs at colleges and malls, occasionally alongside other local talent such at Fat Tony and Freestyle Bully.

[11] The pair later formed a rap group Three Loco along with comedian Andy Milonakis, increasing Riff Raff's popularity by tapping into the two celebrities' fan bases.

[11][21] Some time before the official split Riff Raff affiliated with producers such as Diplo and Harry Fraud, as well as with Queens rapper Action Bronson.

[25] In April 2012, Riff Raff also announced a collaborative album with Diplo tentatively titled Jody Highroller with guests Skrillex, Usher, Soulja Boy, Gucci Mane, Mystikal and Rusko.

[28] The same year he released the album, The Golden Alien, independently in July [citation needed] which feature tracks produced by MikeChekMusic, "Freeze Dried", "Obtuse Angle".

[40] That same month, Riff Raff told Rolling Stone in an interview that leading up to the album's release he would release various "left-over" tracks from the album's recording sessions[41] These notably included the Boi-1da produced "Real Boyz", featuring rappers OJ da Juiceman and Cap 1, as well as "Suckas Askin' Questions" with Lil Debbie and "Shoulda Won a Grammy" with Action Bronson.

[44] The same day the official track listing for the album was revealed, which included previously announced collaborations Mac Miller, Childish Gambino, Paul Wall, Mike Posner and Amber Coffman of Dirty Projectors as well as Slim Thug.

In April 2016, Riff Raff announced a partnership with Stampede Management and BMG, raising US$4 million for his Neon Nation Corporation to invest in music as well as in "movies and talent across the globe to build an entertainment empire.

"[46] Since his second studio album Peach Panther he has released 3 projects with DJ Afterthought starting out with 2016 Halloween mixtape, "BALLOWEEN" featuring Quavo, Skepta, Trae tha Truth, Travis Barker and many more.

On February 9, 2018, Riff Raff and DJ Afterthought released the album Cool Blue Jewels with features from Wiz Khalifa, Chevy Woods, Jimmy Wopo, Young Buck and Project Pat, among others.

On November 9, 2018, Riff Raff released a mixtape titled Tangerine Tiger with guest appearances from Z-Ro, Lil Tracy, Ricki Rich among others.

On April 12, 2019, Riff Raff released his third studio album titled Pink Python with guest appearances from Chief Keef, J-Dawg, and Killah Priest.

Riff Raff premiered his single "Jazzmine" with the Houston Chronicle, a remake of "A Whole New World" from Aladdin featuring Iliana Eve, Jonathan Hay, Aneesa Badshaw, Ranna Royce and others.

[47] [48] On October 25, 2019, Riff Raff released his fourth studio album titled Cranberry Vampire, with appearances from Simon Rex, Andy Milonakis, Chief Keef, and others.

[49] On February 15, 2012, film director Harmony Korine contacted Riff Raff about appearing in an upcoming movie of his, which would turn out to be Spring Breakers.

"[52] There was much back and forth between both camps about the issue, including Riff Raff appearing in a cameo for One Life to Live playing a character called "Jamie Franko".

[56] Riff Raff has a large number of tattoos, including the logos for WorldStarHipHop, NBA, and MTV, which he had acquired during auditions for the 2009 reality TV show From G's to Gents.

"[14] On August 11, 2013, Riff Raff was arrested in Greensboro, North Carolina after police found an open container of alcohol, marijuana, another unspecified illegal substance and drug paraphernalia in his vehicle.

[59] Afterward, a second woman, aged 17 at the time, alleged that in Milwaukee, Riff Raff invited her on his tour bus; according to the accuser, he proceeded to touch her repeatedly while making suggestive comments.