2006 f350 leaking oil now

[RamAirfreak98ss]

well this doesnt look good.

truck has never really dripped oil, never that i noticed.
2 days ago, i noticed while raining, a few drops underneath in the garage.... after a few hours or so.

Today, truck is in the shop for a hitch replacement in the bed, and after 40 minutes, theres 2-4" puddles under the engine. After looking up with a light, there is lots of visible black oil comming down both sides of the rear of the engine/up against the transmission bellhousing. Even the bottom of the exhaust manifolds are wet slightly.

Last week i noticed that the coolant bottle was overflowing, probably overheated enough to bubble coolant out, i realized that the fan clutch is probably failing/failed because when the engine is warm, i NEVER hear the fan spin up fast like it normally did before, yet the engine temps are never "hot"

Does it need head gaskets? has 118k on it now :/