Lifesteal Olaf *never* working? You crazy Zirene
This is going all the way back to season 2, lol, but Lifesteal Olaf was crazy. General build was Mercs or Tabi for defense along with Youmou's Ghostlblade. Stark's Fervor, Frozen Mallet and a Bloodthirster (sometimes 2, though plenty of flexibility with 5th item) along with Summoner Ghost. Was a rather fragile build at range, but the second Olaf landed a single hit and engaged, fight was over. You couldn't outdamage his healing, which topped out somewhere around 150%, with 20% damage reduction (IIRC) and immunity to CC. My very first, but not last Pentakill was with this build. Only major weakness was against kite-y range if they could maintain a slow on you and your ult was down. Was incredibly fun to play.
Haven't played much Olaf for the last 3 or so years so it probably doesn't work well anymore in general, but back in the day man... Lifesteal Olaf was the shizzy, and that's not never