I've had too many phones to list at this point... But I
think it started with a Nokia 5110, possibly even in 1998 (year of its release; I would've been 10yo at the time) but I always got used phones when I was young because new ones were far too expensive... (whereas always upgrading to "new to me phones" would be totally reasonable... ah, the late 90s/early 2000s tech consumer logic)
I went through 5110 - 6110 - 3310 pretty fast in those early days and there were probably others in there. And of course I had many other Nokia phones later over the years.
Here are some highlights though:
Nokia Communicator 9110, I think I had it in exactly 2002 (as 14 year old) because I remember using it in 8th grade shop class. Used of course and at that time it would've been many years old.
P
robably my first "smartphone" - i.e. big screen for the time and ability to do email, browse some websites etc. I'm pretty sure I got it on a whim and ended up basically sidegrading from it very soon because it was way too bulky and the OS didn't support any apps or anything.
Nokia 6600, very common phone in other posts in this thread. Ability to use internet, chat clients etc. Probably had it around 2004, I'm pretty sure I couldn't afford a 600€ phone new in 2003 when I was 15.
Motorola V600, my first and only flip phone. I only got it because it had style. It had a simple job: calls, SMS, and internet hotspot for...
… the smart device I combo'd with the Motorola - a Fujitsu-Siemens Pocket Loox 720. PDA with Windows Mobile. This was the device I would actually use like we use mobile devices today. Large browser window with proper HTML rendering, e-mail, IRC, MSN Messenger, games, nice camera, everything. I liked this combo a lot. Had it probably throughout late 2005 - early 2006.
Qtek 8310, probably my first truly modern smartphone, and one of the first NEW phones. Windows Mobile with multitasking, wifi, real internet browser (MSIE), native MSN Messenger client, etc etc. Everything in a single device. I'm guessing the picture is taken when I got it so early 2006.
Then eventually the tech world changed overnight...
iPhone 1st gen - probably as it was being jailbroken and operator-unlocked in Sep 18th, 2007, 2.5 months after the US release. Bought new on eBay from a random guy in Texas. I registered on eBay for it and it was the transaction that would teach me international shipping and import taxation, among other things. The first iPhone would never be available in Finland. Why didn't I buy directly on release? Simple, had to wait for hackers to make the jailbreak and operator unlock software first... But this is how important that phone was, it was easily worth all that trouble and waiting and was probably the best phone I ever had relative to the time period of the phone. One funny side effect of all the trouble is that not many others had iPhones, in fact I don't think I ever saw any until iPhone 3G's were officially released in Finland much later.
After that it was the modern era of phones for me:
iPhone 3GS - nice phone, didn't need jailbreaking anymore because they'd come up with the App Store, but the plastic body felt pretty cheap.
iPhone 4 - another true upgrade to the iPhone, because of the beautiful metal/glass body and high res display. Really liked that one and there were people around me who swore by their iPhone 4 YEARS after it had become obsolete. Even I had it for more than 3 years, the longest I'd run a particular phone at the time.
Sony Xperia Z1, bought in 2013. At this point I'd had the iPhone 4 for over 3 years so it was time for an upgrade, but iPhones (4S, 5, 5S) were honestly pretty boring upgrades since they looked the same and worked the same, and had no truly progressive upgrades except TouchID. So I decided to try Android for at least a year, which is when a new iPhone would come out with a new design. This year-long experiment basically solidified to me that Android was an inferior OS due to the way none of the Android phone manufacturers are responsible for their Android user experience the way Apple is of iOS. It was buggy, slow to get updates, updates broke stuff, 3rd party software like apps were shit, and the user interface wasn't as polished and thought-out as iOS. But the phone was nice, made of good materials (although I remember it getting more scratches in a year than the iPhone 4 got in 3 years). Also had a nice camera.
iPhone 6 Plus - bought on release in 2014. This was finally the true upgrade to the iPhone for me since 2010 with the phablet form factor, TouchID, fast CPU and lots of RAM, 1080p display with nice quality, camera with OIS, etc.
I'm still on this iPhone today because there hasn't really been an upgrade that I'd consider worthwhile and a no-compromise upgrade. iPhone X was close but the notch is a deal-breaker. I'm probably upgrading next time when either the iPhone 6 breaks, doesn't get software anymore, or there's a new iPhone design with no notch.
And yeah, the iPhone 6 Plus is the longest I've ever been on a particular phone - over 4 years.