Hm.
I’m bypassing the obvious answer, Frangosyriani, because that’s a song that in a sense ended the Classic Rebetika period, and marked the start of the taming of the tradition that brought about laika music.
Songs that I have a lot of time for myself include:
Πέντε Χρόνια Δικασμένος (1934). Music & Lyrics: Vangelis Papazoglou.
stixoi.info: Πέντε χρόνια δικασμένος ( Γεντί κουλέ )
https://youtube.com/watch?v=sFKmVyOZLKI
Been condemned for five years
to Yedi Kule jail.
Had the blues so bad,
I started smoking the bong.
Blow, suck, drag it in.
Step on it and light it up.
Keep a look out for the hillbillies,
them jailers.
Five more years forgotten
by you, my dear.
The guys would light me up
the bong, to cheer me up.
Now I’m out
of Yedi Kule jail.
Fill up that bong
so we can have a smoke,
Blow, suck, drag it in.
Step on it and light it up.
Keep a look out for the alley,
here come two schmolicemen.
Κάν’ τονε Σταύρο, κάν’ τονε (1935). Music & Lyrics: Markos Vamvakaris
stixoi.info: Κάν΄ τονε Σταύρο, κάν΄ τονε
https://youtube.com/watch?v=PZgKSrIzTMQ
Set it up, Stavros, set it up,
light a fire and burn it up.
Give a puff to Mad George,
craftsman and woodworker.
Have a drag, John the carter,
you sly den-dweller.
Give it to our dear Nick,
so he can satisfy his yearning.
Give a drag to our Batis,
the thug and lady-killer.
Έφοδος στον τεκέ (1933). Lyrics: Giorgos Kamvysis. Music: Petros Kyriakos
Why yes, the animation on the video *is* by one Nick Nicholas.