1. SIS + AL [GORE]
4. LEGISLATE [double definition]
8. PENALIZE [PENAL LIES homophone]
9. SO(M)BER [double definition]
11. UNDERGROUND [double definition]
13. SURf
14. N + E + W + S
15. DEEPEST [THE PEST as said by Fantasy Island's Tattoo]
18. E(CO)NOMY [MONEY anagram]
20. JURY [double definition]
22. EVE [double definition]
23. INCONGRUITY [Sticks out like...]
24. P(AID) IN
25. HALF FULL [The glass is half empty or...]
27. LEGENDARY [LEG END pun]
28. AI(D+E)S

1. SUP + PURe + ATE [PUS reversal]
2. SY + NODS
3. LIL [& lit.]
4. LA + ZA + RUS
5. S + WORD BEARER
6. AB + B + ESSES
7. E(RR)OE [EEYORE homophone]
10. KURD [CURD homophone]
12. RHETORICIAN [IN RHAETO-ROMANIC - MOAN anagram]
16. TRICYCLES [THREE LEGS pun]
17. sHOVEl + RING
19. YA(C)K [KAY reversal]
20. JANUARY [RAY JUAN anagram]
21. PIQUED [PEAKED homophone]
22. EX(P)EL [XL as written]
26. FRAu