Up until about a year ago, I was still using my Cowon D2 MP3 player. It was about ten years old. It had the kind of battery life we only dream about these days: 40-something hours a charge. It never even died. I retired it and replaced it with my LG Optimus G Pro smart phone when I upgraded to a Nexus 6P. The G Pro is now the oldest thing I regularly use at ~5 years.
I have a Wii hooked up to a 4:3 Philips CRT tv, but I've only used it a few times this year... so maybe that doesn't count.
Other than that my main work laptop (I work from home) is a giant Asus monstrosity from summer 2011, it is really showing its age and I'm hoping to replace it this year.
Nothing that old...I have a 32" Samsung HDTV that I got in 2010 that I still use as my primary gaming TV. Also an iPod Touch from 2011 that's my main music player. Everything else I cycle pretty regularly.
Before I got the Samsung, my gaming TV was a 12 inch CRT from the 80s. Played 170 hours of Oblivion and a ton of Halo 3 multiplayer on that piece of shit.
I use the same Sony digital alarm clock that I got when I first started waking myself up rather than my parents shaking me out of bed. That was almost 25 years ago and the thing is still in tip top shape. If I wake myself up 5 days a week and conservatively say that I hit snooze 3 times a day, that's almost 20,000 whacks on the snooze button. Never had an issue.
A year or two later I got a Sony stereo for my room complete with 5-disc (5!) CD carousel. It's been a while since I've used it but it's also still kicking as far as I know.
Oh, man I had an Sony alarm clock-radio I bought in 1984 8th grade that I used until graduate school in 1999. It was pretty much my "get up for school" alarm clock throughout all my REAL school years. When I bought it in 1984 I put brown duct tape (to match teh wood grain plastic) on the snooze bar because I learned "snooze" was the enemy. From 8th grade through grad school it was set to annoyingly loud and put on the opposite side of the room, so I was stunned awake and had to run to the other side of the room to shut it off.
Checking my Amazon order history...
I bought a Samsung 55" 1080p LED TV on July 9, 2009 that I've been using every day. It cost $3600 back then. (Before that TV, I was using a Sony WEGA 36" flat screen CRT.) I've been looking at replacing it with a 65" 4k HDR OLED this year for pretty much that same price (not counting inflation).
The next oldest thing I still use is the Blu-ray player (July 18, 2009, before I had a PS3). The combination of the TV, Blu-ray player, and a copy of Planet Earth, convinced my friend to buy a new HDTV (they were still called that) the next day.
My PS3, I suppose. I've had the fat 80gb model sticking around since 2009 and though it has acted up strangely a few times during all these years, it still works good enough to play games without any trouble.
My folks still do have my old alarm clock at their place, a silly Charlie Chaplin thing. That thing still worked last year when I tested it and I think I got it in the early 90's.
Been playing through Fire Emblem on my DS that I got Christmas of '04. But come to think of it, I just used my PS2 (fat, not slim) to watch a DVD. Also, I think I've been using the same alarm clock since 2000. It's kinda scary to see how disposable technology is. On the Waypoint podcast they briefly talked about what happens to TVs after they're disposed of. seemed like a depressing topic.
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