King Von, a prominent figure in drill music from Chicago, was celebrated for his exceptional storytelling ability, a trait that significantly set him apart within the genre. His debut single, "Crazy Story", released on December 6, 2018, rapidly became his breakout hit and established his distinctive narrative style. The song's success was so profound that it spawned two sequels, "Crazy Story 2.0" and "Crazy Story, Pt. 3", all of which feature on his mixtape Grandson, Vol. 1.

The raw and vivid lyrics of "Crazy Story" immerse the listener into the perilous world of street life in Chicago, detailing a planned robbery that spirals into a violent shootout. Von's storytelling is characterized by its intricate wordplay, dialogue insertion, vivid imagery, and pop culture references, creating a cinematic experience for the audience. Mark Braboy of Complex notably praised Von as a "thoughtful, skillful lyricist" whose delivery was "ferocious and resonating," surpassing many of his drill contemporaries. HotNewHipHop further highlighted how "Crazy Story" laid the groundwork for Von to be cemented as one of drill's great storytellers.

A fascinating insight into the creation of "Crazy Story" comes directly from King Von himself. He revealed in interviews that he wrote the song while traveling on a Greyhound bus from Atlanta to Chicago, composing the lyrics without an instrumental. He would later find a beat that perfectly fit the narrative during a studio session. This method highlights his natural talent for crafting coherent narratives, a skill he honed during his time in jail, where he spent years awaiting trial. He mentioned that in jail, "you don't do shit but read, write, and think about the past shit that I did," and reading books likely influenced his storytelling.

The song opens with Von receiving a "drop" – intelligence – on a "flexin' nigga" from Tennessee, facilitated by a "thot" (a woman he manipulates with promises of expensive gifts like Jimmy Choo shoes and a handbag). This immediate plunge into a transactional relationship for street gain sets a gritty tone. The target is wealthy, described as having "bricks, plus his neck is icy and it match his wrist," signaling a lucrative "major lick". The plan involves luring the target to a specific spot, initially "The Wic," but the target, seemingly cautious, changes the meeting to a store. Von, armed with his reliable Glock, prepares for the confrontation, underscoring the constant threat of violence with lines like "I grab my Glock, it been through a lot, but it still shoot like new."

The tension escalates as the target arrives in a new Porsche, pulling up and double-parking but not immediately exiting the vehicle, indicating a level of awareness. The woman, acting as bait, approaches and engages in affection with the target. Just as Von moves to ambush, "crouching like a tiger, like Snoop off The Wire," his plan is suddenly derailed. Rival gang members, "the opps," unexpectedly appear, yelling "What's crackin'?". This unforeseen turn transforms the robbery into a spontaneous shootout, a common and dangerous reality of street life. Von reacts instinctively, asserting his born ability to shoot: "I was born to shoot / I got aim, I'm like Johnny Dang when it comes to chains." He wounds two of his attackers, hitting one in the arm and another in the thigh, emphasizing the do-or-die nature of these encounters.

The song's outro delivers a potent declaration: "Bitch we not from 63rd / This the game, put in work". This line is more than just a geographic reference; it's a defiant statement of gang affiliation and rivalry. King Von was from O'Block, which is located on King Drive between 63rd and 66th Street, an area often associated with the Parkway Garden Homes. The "63rd" he refers to is commonly understood as 63rd and St. Lawrence, home to rival gangs like STL/EBT, who were major adversaries to O'Block. By explicitly stating "we not from 63rd," Von distances himself and his crew from these rivals, reinforcing loyalty and warning potential enemies of the consequences of crossing them. This final assertion encapsulates the brutal realities and territorial pride inherent in the drill scene that King Von so masterfully articulated through his "crazy stories."