Isle of Man (an island and Crown dependency of the United Kingdom in the Irish Sea)

walkman (any personal cassette player)

A transliteration of the German male given name Hermann

(music) frontman

one-on-one fight / (by extension) one-on-one competition or contest

(archaic) red-faced / (archaic) embarrassed, guilty of conscience

have influence through one's reputation, have clout

meet / appear together, costar / compete together in a game or match, face off

facial features

an emoticon