Throughout his career he has been heavily affiliated with rapper Wiz Khalifa and his Taylor Gang record label, also serving as Khalifa's usual hypeman on tour. His first major appearance was on Wiz Khalifa's song "Taylor Gang". Since then he has released various mixtapes such as The Cookout with Khalifa and the Gangland series.

Chevy Woods first began rapping as a child, saying he and his homies would "take instrumentals and rap over it playin’ around." After graduating high school, he attended Robert Morris University in Pennsylvania, where he began getting passionate about rapping.Woods said it became serious at a point, when he "met this dude who had his mixtapes pressed up and ready to go, passing them out." Woods told him "I wanna get down with that." Then he just started writing, "just doin' it straight paper, straight rappin'" under the name Kev Tha Hustla.

He met fellow Pittsburgh, Pennsylvania, rapper Wiz Khalifa for the first time in 2004 through Pennsylvania producers I.D. Labs, who significantly collaborated with Khalifa. They hit it off immediately and shortly formed the group Taylor Gang.He went on to release two mixtapes, The Corner's Correspondent and Animal, in 2008 and 2009 respectively.His first two mixtapes featured collaborations with Wiz Khalifa, Boaz and members of Heavy Hustle Records. Production was primarily handled by I.D. Labs and Sledgren, among others.On September 13, 2010, Woods released his third official mixtape Pilot Shit.

On February 17, 2011, Wiz Khalifa released his ninth mixtape, Cabin Fever featuring Chevy Woods on three tracks "Taylor Gang", "Middle of You" and "Homicide".Then on March 17, 2011, Woods released his fourth mixtape Red Cup Music, which featured guest appearances by Juicy J, French Montana, and production by ID Labs and Mac Miller.He told MTV that the Red Cup Music was "really when I found a style for myself, some laid-back, cool music. Drink a little bit, smoke a little bit."On April 7, 2011, Khalifa released the music video for the Lex Luger-produced "Taylor Gang" track, which ended up as an iTunes bonus track on Khalifa's debut studio album Rolling Papers.The song would end up peaking at number 22 on the Billboard Bubbling Under Hot 100 Singles chart.On April 13, 2013, Khalifa revealed that he would be going on tour in support of Rolling Papers with Chevy Woods and Big Sean.These events resulted in Woods introduction to Khalifa's mainstream audience.Woods then announced that he would release mixtape titled, The Cookout that would heavily featured Wiz Khalifa, in August 2011.

After Khalifa officially founded Taylor Gang Records, Woods was immediately added to the roster. The Cookout was then released on September 24, 2011, the mixtape featured Wiz Khalifa on eight of the eleven tracks, and was produced by ID Labs, Sledgren, Cardo, Key Wane and Big Jerm.The mixtape was met with a positive review by XXL, who praised the production, but said Woods played second fiddle to Khalifa throughout the tape.However, MTV disagreed calling Woods the mixtapes star, also praising his laid back flow.

In early 2012, Woods announced he would be releasing a new mixtape titled Gangland. The dark material would be influenced by Woods early life on the streets, and the television show Gangland.Chevy Woods along with the rest of Taylor Gang Records,Lola Monroe, Juicy J, and Wiz Khalifa covered the May 2012 issue of The Source.Gangland would then be released on June 5, 2012. Gangland would feature Taylor Gang's Wiz Khalifa, Lola Monroe, Juicy J, Tuki Carter, , among others such as, Soulja Boy, Trae Tha Truth, and Young Jerz. Production on Gangland was handled by Lex Luger, I.D. Labs, Cardo, Sonny Digital, Key Wane, Sledgren and Harry Fraud, among others.XXL would also give Gangland a positive review saying, "Over the past two years, Taylor Gang’s Chevy Woods has gradually built up his name with mixtapes like Red Cup Music and The Cookout. Progressing with each release, Wiz’s budding sidekick has shown he can hang high without resting on the back of his co-pilot. On his latest offering, Gang Land, Chevy flies high and gives the world an in depth look into his life as a Taylor Gang aviator."

Following the release of Gangland, Woods begun working on his next mixtape and his debut studio album.From July 26 through August 5, 2012, Woods went on the first Under the Influence of Music concert tour with Khalifa, Mac Miller, Schoolboy Q and Kendrick Lamar in support of Gangland.Then from October 12 through December 6, 2012, Woods toured with the rest of Taylor Gang Records on the 2050 Tour.While on the tour, he announced that his next mixtape would be titled Gangland 2.In mid-2013, he toured on the second Under the Influence tour with Khalifa, ASAP Mob, B.o.B, Joey Badass, Tydollasign, Pro Era, Berner, and Trinidad James.

In late-August 2013, Woods told HotNewHipHop that his debut album would contain production by Sledgren and C4, and that he recently chose the final tracklist for Gangland 2. He also revealed that it would be hosted by DJ Drama.On September 23, 2013, Chevy Woods released the cover artwork for Gangland 2.From October 17, through November 30, 2013, Woods toured North America with Joey Badass, Ab-Soul, The Underachievers, and Pro Era on the fourth annual The Smoker's Club tour.On October 24, 2013, Chevy Woods released Gangland 2 via Taylor Gang Records. The mixtape featured guest appearances by Wiz Khalifa, Juicy J, Trinidad James, Young Scooter, King Los, and Compton Menace among others.On April 18, 2014, Woods released his first retail single "30 Deep" via Taylor Gang. He then announced a retail EP to be released in August or September 2014.Then Woods made two appearances on Wiz Khalifa's third studio album Blacc Hollywood, on "Still Down" and spoke on the intro to the album.Woods upcoming release Gangland 3 is set to release January 27th.