• Matthew Perry as Ted? Oh no. Perry is 15-20 years older than Teddy was at the time - and looks even older and more dissolute. Actually, an Osmond kid would be a better fit. Onassis was barely 5' - a squat, ugly man - not a good-looking 5'11" Arab. A Boris Karloff look-alike would have been better. Katie Holmes is not terrible as Jackie but that has more to do with the hair and clothes than her acting. Was Jackie really that nervous when Onassis was negotiating her dowry with Teddy? Because Ari's estate "settled" with Jackie for $25 million upon his death so she wouldn't contest the will. After 7 years of marriage - not a bad investment of time.