Sylvan LaCue began his music career in 2009 under his then name, QuESt, after taking inspiration from Canadian rapper Drake and his sudden success following the So Far Gone mixtape. He chose the stage name "Quest" but stylized it as "QuESt" after rapper Nas' uppercase "S", saying "Quest is a common name, I wanted to differentiate myself in some way, shape, or form."

After a troubled relationship with his mother, Sylvan moved out of his mother's home at the age of 17 and thereafter, repeatedly moved back in and out of her house.

In 2009, he was the champion of Jermaine Dupri's "Survival of the MCs" competition, beating 660 other hip hop performers and earning a deal with Dupri's newly founded TAG Records. However, months after Sylvan won his deal with TAG Records, the record company folded. Subsequently, Sylvan began releasing content online following the era of the online mixtape circuit, building a solid following under his then name "QuESt."

Into 2011, Sylvan was living independently and was working full-time as a janitor. In late 2011, Sylvan's father moved in with him after being released from jail and convinced Sylvan to allow him to take care of financial responsibilities.

Six months after giving his father responsibility of the finances, Sylvan and his father were evicted on May 10, 2012. Following being evicted, losing his job weeks earlier and giving his father his car, Sylvan almost decided to quit rapping. He also had doubts of success after not getting recognition despite releasing works, contacting individuals in the music industry and performing independently. He decided to speak with his A&R representative where she told him to take his time and not to do anything.

Sylvan moved to San Diego, CA feeling he needed a "change in scenery" after experiencing his hardships. Deciding to take his time, Sylvan decided to tour with rapper Logic on his Welcome To Forever Tour in early 2013. After building a relationship with Visionary Music Group president Chris Zarou, it was announced in August 2013 that Sylvan joined Chris Zarou's record label, Visionary Music Group (VMG).

On September 2, 2014, Sylvan released the Searching Sylvan mixtape. Following its release, The Huffington Post named Sylvan on their 11 Artists You Need To Know For The Rest Of 2014 list, with The Huffington Post stating “[Sylvan] is about to prove himself one of the most promising storytellers in hip-hop" and that Searching Sylvan was not "just one of the best mixtapes or hip-hop releases this year ... [it] is one of the best albums all year". Near the end of 2014, The Huffington Post again placed Sylvan on a list, placing Searching Sylvan #6 on The 15 Most Underrated Albums Of The Year.

In December 2014, Sylvan announced that he had decided to leave Visionary Music Group due to differences with the management, stating that there was "no ill will towards them". Weeks after separating from his previous label, Sylvan created the WiseUp music collective. He returned to Florida to reconnect with friends and family, speaking on an industry panel in the spring before heading to Orlando to prepare his next body of work.

In June 2015, Miami New Times listed Sylvan as one of 5 Miami Artists You Should Know, stating that "he’s been taking Miami by storm since 2009. It's 2015 now, and he’s still going strong."

On September 2, 2015, Sylvan released a statement on his website which announced how he has dropped QuESt as his stage name and will go by his birth name. The statement was accompanied by a featured journal on VSCO which detailed what he had gone through in the past year, such as finding himself as an artist.

"There was this one time, me & my engineer went to this coffee shop we became super fond of. There was this barista I knew that was working that afternoon. We played a new record and she loved it.

She always knew my name was "QuESt", but never heard any of my previous work besides that song. I remember paying for my cup of coffee, and my real name popped up from the card scan: Sylvan LaCue. She said, 'This is your real name?... This fits you a hell of a lot better than QuESt, just saying.' Ironically, I guess I was Searching Sylvan all along..."

Sylvan also announced that he would be dropping a project titled Far From Familiar. The album is a direct sequel to "Searching Sylvan" and is produced by WiseUp's in-house production team, The Marvels. In November 2015, he released The Watcher 3 to herald his return and offer an unapologetic and observant report on the current state of the industry. A little over week, Studio City appeared. Both were received well by fans and blogs alike.

On December 15, 2015, Sylvan announced the EP Evangeline, which was scheduled to be released for free, on December 18, 2015. The EP is a "love story" according to Sylvan, that takes place after the events of his debut album, Far From Familiar.

In anticipation of the new project, Sylvan released Fall From Grace, the first official single on February 4, 2016 via Complex Magazine. The song was originally titled So Help Me God before being renamed the night before in response to Kanye's indecisiveness over his album title. Sylvan revealed the inspiration behind the song on his Twitter following its release.

"I wrote 'Fall From Grace' at the lowest time of my life last year....That song is all about asking God to save me from myself. Imagine feeling invincible & knowing you're doing all the wrong things & thinking all the wrong thoughts. That's what 'Fall From Grace' is."

Far From Familiar was released on April 8, 2016.

In an article released the day before the release of Far From Familiar, Lacue explained his ambitions in an interview with The Fader. He explained that the final track of Far From Familiar, "At What Cost?", was him finally obtaining peace with himself, stating, "I chose to close out with this because it's also the title of my next project". Lacue also said that he was focused on expanding his brand, WiseUp & Co., and that he planned to go on tour in 2016. Read more on Last.fm. User-contributed text is available under the Creative Commons By-SA License; additional terms may apply.