Against All Flags/Buccaneer's Girl is the second pirate double bill from the Pirates of the Golden Age collection that I've watched. Maybe the better disc of the two.
Against All Flags stars Errol Flynn as a naval officer going underground into a pirate island on Madagascar. He is welcomed by captain Maureen "Spitfire" O'Hara, but captain Anthony Quinn is more suspicious - since he is saddled with the name Roc Brasiliano, he has reason to be bitter. On a raiding voyage, they capture an Indian princess (Alice Kelley) who gets all kissy with Flynn, which doesn't sit will with O'Hara.
O'Hara should be the best thing in this, with her flaming hair, her thigh-high boots and her arms akimbo bravura postures - but actually, she's quite stiff. Flynn isn't bad, but maybe not great, and Quinn really does seem P.O'ed to be stuck with such a weak role. This one is just fair.
Buccaneer's Girl is a bit better - party girl Yvonne De Carlo (Lily Munster) is a stow-away on a ship taken by pirate Philip Friend. Put ashore in New Orleans, she joins Elsa Lanchester's "girls' school" and hires out to entertain the quality at their parties. There she discovers that her pirate is also the head pirate hunter of New Orleans, working for Robert Douglas, the richest man in town - whose ships are always the ones taken.
De Carlo is much more successful in this role than O'Hara. She is just as spunky and much less restrained. Perhaps she's just more comfortable in tossed-off genre films. Maybe I just wanted to see Maureen O'Hara take her fists of her hips and slap her thigh, but she never did, darn it!
So, the other two movies in the set were Yankee Buccaneer and Double Crossbones - one a B-movie made on the sets for Against All Flags while Flynn was recovering from an on-set injury, the other a Donald O'Conner comedy. Certainly these movies have the prestige, but the others are maybe more fun. As far as the cheese factor goes, I'd call it a draw.