The Most Captivating Celebrity Court Appearances, From Oprah Vs. Beef to Taylor Swift's $1 Lawsuit

Image via Getty.
Image via Getty.

You’ve asked. We’ve listened. Your cries are answered. We’ve brought back someone very special to join us on this week’s episode of DirtCast.


Madeleine Davies and I have a rollicking good time talking with Jezebel’s very own Bobby Finger about some of our favorite celebrity trials, from the Bling Ring to the time that Martha Stewart did a stint in the clink for insider trading.

Using Taylor Swift’s recent victory against Colorado DJ David Mueller as a springboard for this lively discussion, we revisited some of the more interesting celebrity court cases over the past decade—at least, the less intense ones, like Winona Ryder’s infamous shoplifting trial in 2001 concerning her theft of almost $6,000 worth of merchandise. The CCTV footage of Ryder casually leaving the Beverly Hills Saks Fifth Avenue was absolutely everywhere at the time.

Ryder remained relatively tight-lipped about the incident until recently, when she told PORTER Magazine in 2016, “Psychologically, I must have been at a place where I just wanted to stop. I won’t get into what happened, but it wasn’t what people think. And it wasn’t like the crime of the century! But it allowed me time that I really needed.” For Bobby, Ryder’s statement comes off as “an interesting perspective about rehabilitation” and is a unique and ultimately more honest way of dealing with the repercussions of a crime that, for those who care about these sorts of things, will live in infamy. We also discuss how Martha Stewart’s brand was only strengthened by her insider trading trial, and dig deep into the influence of Oprah.

While celebrities may get special treatment in almost every other area of their lives, the courtroom—in theory, anyway—is a great equalizer. Famous people really are just like us, and while the sentences for celebrities who find themselves in sticky legal situations are often lighter, the fact remains that they, too, must go to court.

DirtCast can be found on Apple Podcasts, Stitcher, Spotify, Google Play, and iHeart Media.

Our show is produced by Levi Sharpe with editorial oversight by Kate Dries. Mandana Mofidi is our Executive Director of Audio. Our theme music is by Stuart Wood. This episode was mixed by Corey Schreppel. Listen to our politics podcast, Big Time Dicks, here.

Senior Writer, Jezebel



I love Wednesdays & this week’s guest is like free extra toppings/gift with purchase - welcome back Bobby!