i’ve had a lot of guitars over the years. my first “real guitar” was a red gibson sg:
this was the time of my life when my rent was $250 and i didn’t know what a savings account was, so i was a bit of a real gear head. i had a lot of amps over the years, too, but my favorite combination was running through an old ampeg v4 (which is technically a bass amp) connected to an emperor cabinet:
special shout out to the marshall jcm 800 and the peavy vtm 120, which i also loved playing with.
i had a pretty intense pedal board too, mostly with lots of fuzzes, phasers, and delays. some of the fuzzes i bought, but i built a few too (shout out BYOC). my favorite sound came from a russian big muff clone and this phaser, which is still the BEST phaser sound i’ve ever heard:
the other expensive guitar i picked up during this time was the j mascis jazzmaster, which became the primary one i played for some time:
then one night my car was broken into and my guitars were stolen along with most of my pedals (long and stupid story but definitely my fault) 
my friend lent me a mexican telecaster he had lying around, and i ended up buying it from him for a couple hundred bucks
after all my stuff getting stolen, i was pretty crestfallen and didn’t have the enthusiasm to mess around with finicky vintage gear anymore, so i ended up selling my amp set up and just got a reissue of the blackface twin reverbs
i was just using this pedal at the time:
then i saved up some money and decided to buy a “real” guitar again so i bought a les paul jr in sunburst:
at the second or third band practice with this thing, the guitar strap broke when i lifted my arms up and it fell straight to the concrete floor and the neck snapped. shortly after this, the band broke up and i went to grad school so i just sold all my guitar shit.
then many many years passed and now i’m finally getting back into guitar again! for a year or so i’ve just been fucking around on this cheap yamaha acoustic
but i’m itching to play “aggressive” music again, so i got myself a cheap little set up coming in. i’m going back to my roots with an epiphone sg
i’m also getting a 20w orange combo–i briefly played with an orange cab back in the day, and i always like the build material. maybe heretical, but i’m getting it in black:
then instead of messing with analog fuzz pedals which are prone to break and fritz up in the weather, i’m just gonna stick to the classics:
it’s nice being a recovering gear head, not only because that stuff seems to be 10x more expensive now than when i was originally buying and selling it, but also because i don’t care anymore.
in the new year i plan to get a cheap audio interface so i can start recording some stuff too and form an ersatz band with some buddies back home. again, it’s nice to be older and do this sort of thing simply for the fun of doing it.