2011–2013 In 2011, Shy Glizzy released his debut project, titled
No Brain, in January. He released his second mixtape,
Streets Hottest Youngin, on October 31. On June 6, 2012, Shy released his third mixtape titled
Law. He was featured by
Complex on its list of "10 New
DMV Rappers To Watch Out For." The
Washington City Papers Ramon Ramirez referred to it as "a well-connected tape [which] sometimes feels like it wants to be a major-label-debut", featuring guest appearances from
Project Pat and
Wale and production from
Beat Billionaire, but described Shy as being "less polished, and more , while his hooks are repetitive and droning but also hungry and catchy." On November 14, 2012, Shy released his fourth mixtape,
Fly Money, an 11-track collaborative project with Jose Guapo. On December 12, he released his fifth mixtape,
Fxck Rap, featuring a guest appearance from
Trinidad James and production from
Speaker Knockerz. On March 16, 2013, Shy Glizzy was listed by
Complex as one of "15 Unsigned Rappers Who Should Get a Deal After
SXSW". On April 3, he announced his sixth mixtape,
Law 2, which went on to be released on August 1, and included guest appearances from the likes of
Migos,
Yo Gotti,
Starlito and
Kevin Gates.
2014–2016 On January 7, 2014, Shy Glizzy was listed by
Fact as one of "10 Rappers to Watch in 2014". On January 20, he announced his seventh mixtape,
Young Jefe, which went on to be released on February 17, and included guest appearances from the likes of
Young Scooter,
PeeWee Longway,
Young Thug,
Plies and
Gudda Gudda. From that mixtape, the hit single "Awwsome" turned into the biggest song of his career and peaked at number 45 on the US
Hot R&B/Hip-Hop Songs chart. It spawned a remix off the record that features
A$AP Rocky and
2 Chainz that grabbed more than 750,000 streams on SoundCloud in the first week of its release. On June 3, 2015, Shy Glizzy was selected as part of the
XXL magazine Freshman Class list. That same day he released his ninth mixtape,
Be Careful, a 16-track collaborative project with his Glizzy Gang collective which included members 30 Glizzy, Goo Glizzy and 3 Glizzy. On August 28, Shy announced his 10th mixtape,
For Trappers Only, entirely produced by
Zaytoven to be released on September 30. It included guest appearances from the likes of
Boosie Badazz,
Yo Gotti and
Ty Dolla $ign. On July 8, 2016, Shy Glizzy announced his 11th mixtape,
Young Jefe 2, to be released on July 15. In a December 2014 interview with
The Fader, when asked about his thoughts on DMV rap, Shy responded "DMV still didn't become a thing. Nobody opened up a lane for DMV rap I opened up my lane. I opened up Glizzy Gang lane, the southeast DC lane." However, in a January 2017 interview with
The Fader, when asked about the state of DC's rap scene, Shy responded "I'm trying to open up that lane so more youngsters can come through. No one else ever opened that door for me I got a whole culture——to put on for."
HipHopDX's Aaron McKrell described it as "an energetic but hollow offering" but praised Shy Glizzy's delivery and "ability to manipulate vocal sonics." He rated the project 2.7 out of 5.
Pitchfork's Sheldon Pearce stated that it "isn't King at the peak of his powers Here, he mostly seems content to roll leisurely through verses" and showed "no sense of urgency." He rated the project 6.9 out of 10. The single "Take Me Away" was released on September 29, dedicated to the memory of 30 Glizzy who was found dead a few weeks earlier. He released his 12th mixtape
Quiet Storm on December 12, which he described as his "best body of work yet." In 2018, Shy Glizzy released his debut
studio album,
Fully Loaded, on October 18, which included guest appearances from
YoungBoy Never Broke Again,
Lil Uzi Vert,
Young Thug,
Gunna, and
Rick Ross. The album received positive reviews and peaked at number 35 on the US
Billboard 200, selling 14,446
album-equivalent units in the first week. It was announced that Glizzy will embark on nationwide tour with Atlanta rapper Gunna on his
Drip or Drown 2 tour. In an April 2019 interview with HipHopDX's Daniela Evgenivna, Glizzy announced he would be releasing his second studio album titled ''Covered 'N Blood
on April 19. He described the album as being more personal than the feature packed Fully Loaded'' stating "It's a really deep album. A lot of my music is like a diary. This one is about what I've been going through the last few months." On April 10, 2020, he released the single "Lonely Vibes". He released the song "Right Or Wrong" with
Lil Uzi Vert on June 19. On September 18, 2020, Shy Glizzy released his new project,
Young Jefe 3. It was preceded by a video for "Forever Tre 7", featuring No Savage, a new signee to Glizzy's label, Glizzy Gang Records, an imprint under
300 Entertainment. ==Personal life==