BIO  Around the age of seventeen, Crooked I started an independent record company called Muscle Records with professional football players also from Long Beach, Chucky Miller and Leonard Russell. It's not known how many songs were recorded, and the music recorded during this period still remains unreleased to this day. This is when he caught the attention of Noo Trybe/Virgin Records, and landed his first record deal in 1995.

Crooked I originally got his start appearing on compilations released by Big C-Style's record label, 19th Street Records, such as 19th Street LBC Compilation and Straight Outta Cali. He also appeared on the soundtracks to movies such as Ride and Caught Up, where he collaborated with Snoop Doggy Dogg, Tha Eastsidaz, and The Luniz. At the time, Crooked I was still signed under Noo Trybe/Virgin Records, who handled distribution for 19th Street Records. Business was going good, but for unknown reasons, Virgin Records decided to get rid of their urban division, otherwise known as Noo Trybe, and Crooked I was out of a record deal.

Crooked I was later contacted by Big C-Style and Daz Dillinger to form DPG Records, which was originally going to be a sub-label under Death Row Records at the time. Crooked was going to be 20% owner of the label, and the first act released as well.Daz left Death Row Records to run DPG Records independently, but rather than go with Daz, Crooked was trying to figure out his options.

Crooked I also had talks of signing to Dr. Dre's Aftermath imprint, but Dre wanted to release Chronic 2001 and Eminem's Marshall Mathers LP before releasing Crooked. He also had talks with other major record labels who wanted to sign him, but they too were waiting for Dr. Dre's Chronic 2001 album to be released before they would consider signing another West Coast MC. It was around this time that Crooked I re-negotiated the original deal he had with DPG Records/Death Row Records as a solo artist deal with just Death Row Records.

Death Row's Second Dynasty
While on Death Row, Crooked I appeared on a number of compilations, such as Too Gangsta For Radio and Dysfunktional Family, and appeared on various releases, such as Tha Dogg Pound's 2002, Ja Rule's The Last Temptation, and 2Pac's Nu-Mixx Klazzics. He also recorded two albums, Untouchable and Say Hi To The Bad Guy, both of which were unreleased due to various label issues and industry politics. He did manage to release a mixtape along with Death Row's then in-house producer, Darren Vegas, called Westcoasanostra Vol. 1 in the Spring of 2003.

The Start of a New Dynasty
By 2004, Crooked I's album had not been released, Suge Knight was constantly in and out of jail, and Crooked I's contract had expired by November 2003. He left Death Row in early 2004 to start his own label, Dynasty Entertainment.  It wasn't long after that when Crooked I signed a distribution deal with Treacherous Records/Universal, but more legal trouble from Death Row surfaced, and Crooked I had to stop production for his then titled album, Mama's Boy, which was actually going to be the name of Crooked's second release under Death Row Records. Later on the title of the album changed to Mama's Boy Got a Loaded Gun. In the meantime, Crooked I released the online mixtape, Young Boss Vol. 1 through his official website. The mixtape received critical acclaim throughout the underground Hip-Hop circuit, garnering an impressive "XL" rating by the Hip-Hop publication, XXL Magazine.

After the legal matters settled, Crooked began recording again, and prepping the release of his documentary Life After Death Row. He appeared on compilations such as Yukmouth's United Ghettos of America Vol. 2, Sway & King Tech's Back 2 Basics, and on fellow Treacherous Records label mate K. Young's debut album, Learn How To Love[7]. In 2005, the name of Crooked's debut album changed to Boss Music, and he created a buzz with the song, "Boom Boom Clap" in the summer of 2005. He also recorded two songs with producer Scott Storch, "Cali Boyz" and "You're So Bad". In 2006, he released his heavily anticipated mixtape, Young Boss Vol. 2 hosted by DJ Skee, and his DVD, Life After Death Row, followed later that Fall.

Hip-Hop Weekly
Crooked I started the Hip-Hop Weekly series via the internet. Every seven days he released a new track over various hip-hop beats of old and new instrumentals. His ability to personally connect with his fans through his Hip-Hop Weekly series is evident since he would fulfill beat selection requests as well as give shout-outs over any given track to fans who requested it via his MySpace page. The Hip-Hop Weekly series began on April 4, 2007 and ended on April 3, 2008. Wickliffe generated so much of a buzz with the Hip-Hop Weekly series that he was featured on the cover of the December/2007 issue of XXL (magazine) for a second time, this time as part of XXL's Freshmen 10.

Crooked I, along with DJ Felli Fel and DJ Nik Bean, released St. Valentine's Day Bossacre on February 14, 2008. Although it's called a mixtape, it consists of all new tracks by Crooked I, much like Young Boss Vol. 2, and boasts guest appearances by Royce Da 5'9", and Roscoe Umali, with production from DJ Felli Fel, Rick Rock, Komplex, and MG. The February 2008 issue of Ozone West reviewed St. Valentine's Day Bossacre and rated it 4 slaps out of 5.

Two more mixtapes were released in 2008 by Crooked I, The Block Obama: Hood Politics and Block Obama II. The Block Obama was originally going to be hosted by DJ Whoo Kid and DJ Strong, but ended up being released un-tagged without a DJ, and for free download on the internet. Block Obama II was released on the day of the 2008 Presidential election, this time for sale on CDBaby, iTunes, Amazon, Rhapsody, Napster, and other online retailers. Block Obama II also boasts guest appearances from Dynasty Entertainment artists Horse Shoe G.A.N.G. and Sauce The Boss, in addition to Knoc-turn'al and production by Jim Gettum, Komplex, and Rick Rock.

The Slaughterhouse
Joe Budden reached out to Crooked I, Royce Da 5'9", Joell Ortiz, and Nino Bless for a track titled "Slaughterhouse" on his digital release, Halfway House.  Based on the reception of the track, they decided to form a supergroup, minus Nino Bless, and named it after the first song they made together. They released numerous songs throughout early 2009, building a buzz for their self-titled album, which was released through E1 on August 11, 2009.  The album features production from Alchemist, DJ Khalil, Mr. Porter, Streetrunner, plus guest appearances from Pharoahe Monch, K. Young, and The New Royales.

On February 27, 2009 in Long Beach, California, Crooked I was allegedly shot at during a conversation with a fan. The conflicting early media reports on the incident in the following hours initially left people worried and uncertain on his condition, but he has since confirmed to MTV News and other media that he's alive and, while mentally distracted, physically well. Crooked I has declined to further elaborate on the incident, citing where he's from its against the code of the streets.

On November 10, 2009, Crooked I released a digital-only solo EP, Mr. Pig Face Weapon Waist. “It’s a spin off of my Slaughterhouse alter ego,” he said of the odd title, “cause I come out on stage with a pig mask and a Dickie suit on.” The EP also boasts guest appearances from Snoop Dogg, K. Young, M.O.P., The Horseshoe G.A.N.G., and of course fellow Slaughterhouse members, Joe Budden, Joell Ortiz, and Royce Da 5'9".  In addition to production from Komplex, Scram Jones, Streetrunner, Frequency, and P. Silva.

On August 17, 2010, Crooked I released yet another EP, titled Planet C.O.B. Vol. 1, which features production from Rick Rock, Komplex, and more.

On December 1, 2010, the first single for Crooked I's official debut solo album, Million Dollar Story was released on iTunes titled "Villain", which features Gracie Productions recording artist Sally Anthony.

On January 12, 2011, after months of speculation, Slaughterhouse officially signed to Shady Records, along with artist Yelawolf.

On March 21, 2011, Crooked I released the Million Dollar Story EP, available for purchase through iTunes, to tie fans over until the album is released. It features two brand new songs and two previously released tracks.

On July 12, 2011, the compilation Planet C.O.B. Vol. 2 was released digitally, and for a limited time was available on CD through Crooked I's official website. Unlike the previous installment, which was an EP by Crooked I, this album features songs by all of the C.O.B. affiliates, such as Horseshoe G.A.N.G., Sauce Tha Boss, Coniyac, and more. To keep the momentum up for the C.O.B. movement, Crooked I brought his official clothing line to the internet.

On December 13, 2011, Crooked I released the digital EP titled In None We Trust - The Prelude, which includes guest appearances from Jay Rock, Glasses Malone, Mistah F.A.B., Horseshoe G.A.N.G., Coniyac and K. Young.

EPs
2008: Block Obama II
2009: Mr. Pigface Weapon Waist
2010: Planet C.O.B. Vol. 1
2011: Million Dollar $tory EP
2011: In None We Trust - The Prelude EP

Filmography
    - 2004: Bank Brothers
    - 2005: Slumber Party
    - 2006: Life After Death Row