Fit to Fat: Oprah Edition Her weight has cycled a lot but her thinnest/fittest moment was probably in the late 1980s to 90s while she ballooned up again up until 2013/2014 before losing a little again slowly(but still obese). So I present Oprah 1998: Photo 1 Photo 2(Both from Vogue) Oprah 2013: Photo 1 Photo 2