It's a fun and interesting watch. He's never played it before but he has played Black Mesa previously so he's up to speed with the story so far and seeing his reactions to everything is fun.

While he's obviously an experienced gamer, he's not much of a PC or FPS guy so he often shoots and moves like a grandpa, which is both amusing and infuriating.

This playthrough does make me realise how old Half-Life 2 is in terms of its design while watching Woolie constantly getting lost in every single room. HL2 came out in the PS2 era, and while it was very innovative it predated a lot of the streamlining that became standard when consoles became the main target platform for FPS games in the following generation. There's no waypoints or objective markers, no glowing outlines around important doors, vents or buttons, no NPCs barking directions in your ear. The game isn't afraid of letting the player get stuck in a room for five minutes.

All the other Valve games afterward made sure the player always knew what they were supposed to do and where to go, most notably in the Left 4 Dead games