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Despondant figure inEarly English histotical period(6)

S?y?r?

Friend mostly having small amount to drink? Yes and no(7)

Tosspot Ithink but not fully sure why. Tot (small drink) but what about the rest.

Eeyore

E E Yore

Eeyore? gloomy donkey, pal of Winnie the Pooh

possible parsing
EE - early English
yore- long ago period

Friend - Tosh - 'mostly' Tos
Small amount - Spot

A bit tenuous

That sounds ok, Mamya!
Good one!

Thank you