19. T.J. in The Object of My Affection (1998)

Macht stars as T.J., a man struggling in an inconvenient love triangle that pits him against his best friend, played by Jennifer Aniston. The T.J. portrayed by Macht brings out just the right doses of charm and vulnerability as captured in unrequited love and friendship. Macht delivers a well-balanced performance playing a man out of his depths in relationships. The chemistry shared between him and Aniston in the film's emotional arcs makes his inner conflict both relatable and admirable.
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Edited by Zainab Shaikh