Repeated thanks to those who submitted clues for WG 60, and apologies for the long delay.
My judgments are below. The winner is exposed at the end.
Luciano
---------
Duke:
Part of hairdo's eventually natural (5)
SEVEN: hidden; def = natural
-- Fair enough wordplay and definition. I at first struggled to find 'natural' (noun) as an alternative to 'natural number'. However, 'natural' (noun), I discovered, can also mean ' a throw of 7 or 11 on the first cast in craps'. I know that Duke (or 'The Duke') is a gambling legend in Reno and Atlantic City, and presume that this is the meaning that he intended. With all that said, the surface reading does not read naturally ('eventually natural?').
Number it takes to tango with Oscar? (3)
TWO: T + W + O; def = number it takes (by implication)
-- 'to' isn't doing anything, really, but I like this a lot all the same, even if it is a bit transparent.
Blackjack broke, yet went on (6-3)
TWENTY-ONE: YETWENTON anag; def = blackjack
-- My only beef with this is that I'd much rather 'broke' be 'broken' (though apparently 'broke' is a rather antiquated past participle of 'break').
---------
Steve:
Head of state put on uniform for Cardinal (5)
SEVEN: S + EVEN; def = cardinal
-- For some reasons, my dictionaries smile more on 'cardinal' (noun) for 'cardinal number' than they do on 'natural' (noun) for 'natural number' (as in Duke's clue above). This clue works very well in all respects, not least for the believable surface reading.
Naughty character? (4)
ZERO: as in 'the naughties'
-- Imaginative play on naughty/naughties. 'character' as the other half of the clue doesn't quite please me as much.
---------
David:
Legs (6)
ELEVEN: ref to number eleven in bingo
-- A question mark might have been advised. Otherwise, this is good (on the understanding that the solver knew the theme of the competition).
Caught out? Possibly, or possibly not (6,3)
TWENTY-TWO; ref to CATCH 22 and its paradoxical nature
-- Lots of potential with 22 in this context. I feel that this is just a bit vague, however
---------
Rob:
Leave zero, pass fifty, and generate a much bigger number (6)
GOOGOL: GO + O + GO + L; def = a much bigger number
-- My inability to understand this clue was entirely my (and, of course, Google's) fault. The wordplay is good, as is the definition. The surface reading is a bit hyperbolic (that's quite a leap from 50), but there you go.
---------
Bonus clues:
Duke:
Crew dined on ears? (5)
EIGHT: ATE homophone
-- Very good.
Prince's party time puts "Smart Co-worker" on the tail of prime under-twenty (8, 10)
NINETEEN NINETY-NINE: (agent) 99 after 19; def = Prince's party time (ref 1999 by Prince)
-- Of course, I'm much too young to remember this song, but my grandmother confirmed that it was something of a thing during the last century. A bit obscure with the Agent 99 reference. The surface reading's Prince Andrew allusion is a bit tenuous, though his guilt, as far I see it, is somewhat less so.
--------------------------
The winner is Steve with his 'seven' clue. Duke is second ('two'). Rob is third ('googol')