When did his career die?

Probably around the time he stopped even pretending to give a crap, used body doubles for just about anything where you couldn't see his face, couldn't be arsed to do his own ADR, and struggled to get a black belt that fitted him.

Under Siege 2 (1995) was his last popular movie in the theaters.

I don't think I've ever seen a movie he's in.

He was slipping all throughout the 90's with his first big stumble being his directorial debut with ON DEADLY GROUND. He recovered somewhat but his next few movies were underwhelming in terms of box office. After GLIMMER and FIRE DOWN BELOW, he ended up in his first straight-to-video movie THE PATRIOT which was a bad sign of things to come. He also kept putting on more and more weight.

Then came EXIT WOUNDS, which was kinda his second-to-last chance. He slimmed down for the role and cooled-up his image, aided by acting against dorky co-lead Tom Arnold while having some macho scenes against DMX etc. The movie was a modest hit and seemed to be bringing him back.

Then whatever good-will he generated with that, he lost with the crappy HALF PAST DEAD right afterward (and he was back to putting on weight and not caring again), and then it was back to straight-to-video jail for the remainder of his career.

His absolute last chance came with self-parody in MACHETE, which he did well, and he could have segued into a career as a villain or character actor, particularly if he would have gotten over his feud with Avi Lerner and done THE EXPENDABLES, but instead he wanted to stay a star even it it meant low-budget straight-to-video garbage... and so that's where he stayed.