14 Streets Of Philadelphia

14

Was hoping for a 'nick' there

14 - that was a nice cryptic surface. Kept thinking of punch bags (which no doubt was the cryptic intention of course )

sounds good that aspro

1.  Hardy eater (CLUE Hardy is an actor's surname in this instance plus somewhere you would eat, 90's hit, female singer)

2.  Desperate for the loo - I CAN'T WAIT

3.  Cards at Clacton - SEASIDE SHUFFLE

4.  So fast yet haven't stopped dancing - SPEEDY GONZALES
5.  Napoleon in the gloaming - WATERLOO SUNSET

6.  Teaching Marlene's baby (who teaches plus what was the name of Marlene's "baby" Great Dane, 70's hit)
7.  Hydraulic jelly (Hydraulic is a type of what? plus jelly is another word which can be used for what?)

8.  Debt-free antlers - BLACK VELVET

9.  "Let's Be" shocked (what might shock you? plus Let's Be was said by a TV cook in an unusual location to much mirth, when you get what was said in full, it should lead you to a hit from the 80s)

10. Prickly printing - PAPER ROSES
11. Shrapnel needs a scrub - DIRTY CASH
12. Buds in floods - FLOWERS IN THE RAIN
13. Here's the dotted line - SIGN YOUR NAME
14. Sly pounded them - STREETS OF PHILADELPHIA

15. Hush, Tom was on tiptoes (who or what cartoon character is Tom, 70s hit)
16. Chillblains on show (how would you see someone's chillblains, late 60's track from a band which was an answer in yesterday's quiz)
17. Quivering in Cumberland (what is Cumberland?, 70s hit, recently deceased)

18. Baker, Lime, Cannon and Coventry - STREETS OF LONDON

19. Phoebe's feeling nostalgic (earlier answer confirmed you had the right Phoebe, it's a hit from the 60s though, think of another way of saying nostalgic)

20. Albert was a hard man - HANGIN' TOUGH

17. COWARD OF THE COUNTY Aspro

I thought of this earlier but dismissed it, but after your additional clue square:

9. Electric Avenue

(Let's be having you - 'avenue' - ooh, that hurts!  )

15 - Cat's In The Cradle

15. good but not right, what would the cat do on tiptoes?

19 Those Were The Days My Friend.

Yes Aspro, so put them together and come up with a 70s hit

15 The Cat Crept In

15. THE CAT CREPT IN raspberry, UL Aspro did all the ground work

number 1 driving me insane

plus Thomas...

got it. toms diner

1.  Hardy eater (CLUE Hardy is an actor's surname in this instance so you need the christian name plus somewhere you would eat, 90's hit, female singer)

2.  Desperate for the loo - I CAN'T WAIT
3.  Cards at Clacton - SEASIDE SHUFFLE
4.  So fast yet haven't stopped dancing - SPEEDY GONZALES
5.  Napoleon in the gloaming - WATERLOO SUNSET

6.  Teaching Marlene's baby (who teaches? plus what was the name of Marlene's "baby" Great Dane, already been mentioned on here, 70's hit by one of the Motown greats)
7.  Hydraulic jelly (Hydraulic is a type of what? plus jelly is another word which can be used for what?, late 80's one-hit wonder)

8.  Debt-free antlers - BLACK VELVET
9.  "Let's Be" shocked - ELECTRIC AVENUE
10. Prickly printing - PAPER ROSES
11. Shrapnel needs a scrub - DIRTY CASH
12. Buds in floods - FLOWERS IN THE RAIN
13. Here's the dotted line - SIGN YOUR NAME
14. Sly pounded them - STREETS OF PHILADELPHIA
15. Hush, Tom was on tiptoes - THE CAT CREPT IN

16. Chillblains on show (how would you see someone's chillblains, late 60's track from a band which was an answer in yesterday's quiz)

17. Quivering in Cumberland - COWARD OF THE COUNTY
18. Baker, Lime, Cannon and Coventry - STREETS OF LONDON

19. Phoebe's feeling nostalgic (earlier answer confirmed you had the right Phoebe, it's a hit from the 60s though, think of another way of saying nostalgic, last word of the hit is Friend)

20. Albert was a hard man - HANGIN' TOUGH

6 sir duke?