In 1997. I bought a used GSM phone, think it was an Alcatel HC 400, and a pre-paid SIM for it. It was OK but there were some issues with it, such as the battery not having a perfect fit so the phone would occasionally switch off when having it in the pocket. I fairly quickly went on to other phones.
The most annoying phone I've had was a Philips Diga, circa 1998. There were many usability issues including that it was way too easy to accidentally call the emergency number.
The phone longest in use I've had was an Ericsson T65. I bought it in 2002 and used it until around 2008. Durable and good-enough feature set.