Sorry, I don’t have knack like you do, for medleys, but I’ve always wanted to do one for songs that have “ September” in the title. A few that come to mind :

1. “September” by Earth, Wind & Fire
2. “September Skyline” by Single File
3. “Maybe September” by Tony Bennett
4. “Pale September” by Fiona Apple
5. “The September of My Years” by Frank Sinatra
6. “September Morn” by Neil Diamond
7. “September Gurls” by The Bangles
8. “Come September” by Natalie Imbruglia
9. “September When I First Met You” by Barry White
10. “September Song” by Frank Sinatra
11. “Wake Me Up When September Ends” by Green Day
12. “See You In September” by The Happenings
13. “September” by Daughtry
14. “September” by The Shins
15. “September Night” by Van Morrison
16. “September Song” by JP Cooper
17. “September Grass” by James Taylor
18. “September Sun” by Type O Negative
19. “September” by Sweet & Lynch
20. “September Gurls” by Big Star

I’m sure some of you can think of a few more too.

Here’s my and my sax playing partner’s rendition of September In The Rain. The keyboard used in a Keyron Audya.