It's difficult to speak about the Hollywood without mentioning its owner, Doris Goddard. This is partly because her paraphernalia is plastered onto one of the walls, an intimate shrine to her history. (Goddard emerged from slums of Glebe to become a successful film star, performing alongside big names like Katherine Hepburn and Bob Hope.) Another reason might be that she is often in the pub herself, occasionally for one of her renowned midnight performances.
The hotel itself is perfectly suited to an ex-Hollywood starlet. Nestled amongst the deco era buildings of Surry Hill's long vanished film industry (including the heritage listed Paramount Building), all the right details are in place: from a curved wooden bar to antique toilets. That said, there's nothing fussy or intimidating about the joint. Bar staff are friendly and relaxed. The menu consists of chips in wooden bowls and cheese platters, which are more nostalgic than fancy. And the best beer on tap is the Hollywood's own lager.
While the cosy atmosphere is all part of the charm, it's also the only limitation. I'd suggest you turn up early and take over a table, or perhaps duck in for a cheeky afternoon's beers and snacks. When this place gets busy, it gets busy - and with good reason.