Clue: English playmaker Jack heading for nightclub in drag (7)
Answer: OSBORNE
Explanation: Definition: English playmaker
 OS(abbrev. for "ordinary seaman", a sailor/Jack) + [ **1st letter of**(heading for) "nightclub" **contained in**(in) BORE(a drag/a tiresome situation or activity) ].
Answer: …, John, English playwright/playmaker, if you like, best known for his play "Look Back In Anger".