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Expertise in buckling swashes (13)

Marilyn Monroe whips the dole office into shape then spends the money fencing with a jeweller of some repute? (13)

Norma (Jeane) whips DSS

Steely belligerent Nazi enforcer closing in on tip-off (9)

steely belligerent: def
Nazi enforcer: SS MAN
tip-off: WORD

Inigo Montoya, for one, has brief conversation aboard ship (9)

For Princess Bride fans only. This would be after be became the Dread Pirate Roberts, of course.

Brief convo = word, "aboard" = the usual "in between the S's", man = ship

Wasn't it Westley who was the Dread Pirate Roberts?

At the very end Westley offered the gig to Inigo.

https://www.youtube.com/watch?v=IIbeFgaYTNs

I had forgotten. Apparently that was only in the movie:

https://en.m.wikipedia.org/wiki/Dread_Pirate_Roberts

After delivering rabid oration, Romans whip dross into a frenzy, resulting in gladiatorial spectacle (13)

(ROMANSWHIPDROSSINTOA)* - (ORATION)*

A more concise version that replaces #29

Delivering rabid oration, Romans whip dross into a frenzied gladiatorial spectacle (13)

(ROMANSWHIPDROSSINTOA)* - (ORATION)*