His 50-60-hour run is close to the time I've spent on my first playthrough, rolling away from anything that moves. Starting with your bog-standard broadsword, he clung onto it all the way through Champion Gundyr, at which point the Priestess Ring allowed him to swap in Astora's Straight Sword. The Cloranthy, Flynn's and Lloyd's Sword rings completed the set.
There's a playlist of every bossfight, minus the abortive attempts. It's particularly maddening to see Tolomeo run circles around the Nameless King, one of the most alarmingly vicious bosses in the game. His admission that Soul of Cinder alone took about 15 hours to beat makes me feel marginally better about myself.