I want to know….when exactly did Dylan start wearing the famous Boston Red Sox hat consistently? We can see in a Jan 30 ’98 quick video that he has the “B” hat but idk maybe it’s just me but it looks different than he wore in Hitmen for Hire. We know he took out the “B” logo and sewed It onto new hats, so is that one of them? But when did he exactly start like wearing hats backwards ever? Do you think he ever wore his hat forward? When did he get really tall? Junior year?

We don’t really have any documentation that mentions for certain as to when Dyl began his affinity with the Boston Red Sox team and began to wear the “B” ball cap.  Dylan played Little League as a kid, and apparently played very hard and competitively to win and when his team didn’t or he had to sit out, he was crushed.  This demonstrates his extreme love and passion for the sport and being dedicated to his team winning as if the weight of it depended solely upon himself. I would imagine he would’ve begun to start collecting Baseball cards at a certain point in Elementary school and resonating with certain players while watching them on tv or going to a game with his dad.  So, I’m going to say he probably got his first official Boston Red Sox ball cap in his latter Elementary school years and wore that ‘first’ hat through middle school until it was ratty and tattered.  Rather than chuck the entire hat and get a new one, his insisted tradition and solution seemed to become him selecting a new replacement hat (with another team he liked) and having mom sew the “B” on the ‘back’ of the new hat. The “B” itself was the totem, his lucky piece, you could say?  It reminded him of personal ‘happy time’ past memories.  There is a certain sentimentality about Dylan in regards to keeping certain personally significant touchstone items with him throughout his life, on his being, that remind him of a certain something in his past.  I go into detail about this

idiosyncrasy of his “B” baseball cap here.

Dylan does wear his signature baseball cap forward in this shot which appears to be circa early middle school years – playing drums in a band with Brooks Brown.  At some point in the ‘90s, the anti-fashion became about wearing the ball caps backwards to look more against-the-grain of mainstream style. 

I think he likely shot up in height quite noticeably between his Freshman to Sophomore years. My guess.

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Quirks: The idiosyncrasies of DBK

Boston Red Sox / Colorado Avalanche ball cap

Dylan’s favorite baseball team was the Boston Red Sox, and he was often seen wearing a baseball cap with the team’s emblem. Dylan had a sentimentality about him. There were certain personal items he wore religiously as they seemed to signify happier times in his past or childhood. Story has it that the cap had to be replaced several times over the years because it would become so worn out. Each time he’d replace yet another tattered or out-grown cap, he’d transplant the “B” from a former cap on to another. In the last incarnation of his signature trademark hat, the single letter was sewn on the back of a non snap-back black, Colorado Avalanche ball cap. Unlike probably most of the kids at CHS that wore a variety of caps depending on their mood, this was the only baseball cap he wore which combined two of his beloved sports teams for baseball and hockey all in one hat. He would be found dead in the library of Columbine High School in 1999, in a pool of his own blood – with the same hat lying a few inches away from his head – a self-inflicted gunshot wound to his left temple.