Ok, here is my attempt.
1. Clancy
2. Dr. Nick Riviera & Dr. Marvin Monroe
3. Kelsey Gramar
4. Barney (but Homer ended up going)
5. Maggie Simpson
6. Hershal Krustophskey (spelling?)
7. T-Shrit
8. Malibu Stacy
9. Waillen Smithers
10. Seargent
11. Flaming Homer(Moe)
12. Jay
13. Matt Groeneing(spelling?)
14. Futurama
15. ?
16. ?
17. Radioactive Man
18. Kent Brockman
19. Sector 7-G
20. "Bleding Gums" Murphy
21. Mel Gibson, Jerry Springer, Stephen Hawking, Bette Midler, Alec Bawldwin
22. The old tramp who gets a gold house and dragg car
23. Evergreen Terrace
24. Sending Our Love Down The Well(better, if sung by Meat
)
25. Shelbyville
26. Blow Fish
27. Hans Sprungfeld, murderous pirate
28. Lurlene (?someone?)
29. ?
30. ?