My absolute favorite system of all time, handheld or otherwise. Growing up with the PS1 as my first console and the PS2 as my most played console of that gen, the idea of a Playstation on the go was mind-blowing, especially since I didn't get a DS until like 06-07. My concept of handheld games was still limited to what a GBA could output, so seeing games that felt like they belonged on my PS2 on a handheld was nuts!
I begged and begged but could never convince my parents to get me one. Then in 8th grade my parents sent me across the country to visit my great grandmother and some extended family over a long break. Since I was going alone my mom sent me with "emergency cash" that I was supposed to my great grandmother once we landed. When she handed me the cash though my brain completely shut off and I was not listening to a word she was saying anymore, I just assumed the cash was for MY personal spending (I had never held over more than like $20-40 in cash at once before, really felt like I was gonna retire at 13 haha). Needless to say, I bought myself a PSP with Resistance Retribution and Monster Hunter Freedom Unite on that trip. My mom was furious when she found out and I def got what was coming to me, but when the dust settled, I had no regrets.
That thing carried me for the next 6 years of my life. It was my gateway into console modding and became my go-to emulation device. I made countless friends and it would end up being the first handheld I ever played games with other people on as well as the first non-PC system I owned that I played online via the internet (played 360 at a friends house prior but I didn't own one yet). It was my MP3 player before I had a smartphone, it was my mobile internet browser, I even got the camera on sale at a Gamestop and it became the first camera I ever owned and used! It was also the first region-free system I had ever owned and I remember just how amazing it felt when a Japanese exchange student lent me his copy of Monster Hunter Portable 3rd, Initial D (I don't remember which one) and this really cool 3D arena fighting Magical Girl game I can't remember the name of. Shoutouts to you Atsuki, you really saved me by letting me put my name on your history midterm project

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I could keep gushing and sharing stories about that system until I reached the character limit and then some. From Metal Gear Solid Peace Walker co-op shenanigans in summer school to nights where I stayed up grinding in Monster Hunter until my school alarm went off, that system was my everything for quite some time. As much as I adore the Vita, I still value playing PSP games on original hardware, nothin can replace that feeling.
It was lightning in a bottle, no other system is ever gonna feel as ahead-of-its time and become such a massive part of a kids life ever again. Its also a big reason I adore the DS/3DS. Before everyone was addicted to smart phones and it was normalized for kids to have them in elementary school, I had countless friends that spent tons of time drawing, making silly videos and playing games on their handhelds. It helps that hardware occupy such a special place in someone's heart.