Reese Witherspoon’s Hello Sunshine is a major player in Hollywood now. In the last three years alone, well, you know about the success of Big Little Lies, and The Morning Show, and Little Fires Everywhere just finished late last month. She’s producing Daisy Jones and The Six. She has several other book adaptations in pre-production. And her work is elevating female creatives both in front of and behind the camera. 


Whatever has been said about Reese Witherspoon over the years, she’s always had the reputation for being a hard worker, for being a go-getter, for being Type A, which is what she called her production company. Like Tracy Flick only not morally corrupt, although there’s been a revision on how we read Tracy Flick in the last few years, especially in reaction to how female politicians are inevitably always compared to her. Tracy obviously was imperfect, in ways problematic. But there’s also a more nuanced take about the source of her resentments, what shaped her, and what’s undeniable is that she’s a lot more complicated and nuanced and layered than the “oh what an annoying bitch” take that was the collective initial reflex. 

What Reese and Tracy do have in common though is that they believe in themselves. As she told CBS This Morning this weekend via PEOPLE:

"I will put in the hours and I bet on myself. I'm my own lottery ticket," Witherspoon said. "I always think that, you know. If no one else shows up, I know I will show up and I know I will do the work."

This is also what Jennifer Lopez said a few months ago. “I bank on myself”– and it’s one thing to make the statement, it’s another to actually follow through. I have problems “betting/banking on myself”. Self-doubt is a powerful force. 


It helps though, as Reese explains, when you’re betting on yourself for more than just yourself. 

"I really want to change things. I see younger women in our industry and I want them to have a better experience...I want to see that they have a beautiful idea of what the future could hold."

She, of course, was once a young woman in the industry. Next year will mark her 30th year in the business and her first acting credits. It was in the late 90s though when Reese really became a name. And, since we’re doing the Gossip Nostalgia thing today, why not continue with a flashback to Reese 20 years ago, pretty much this week.

In May 2000, Reese Witherspoon and Ryan Phillippe attended the Blockbuster Entertainment Awards together (OMG Blockbuster, when was the last time you used that word in reference to Blockbuster as in where you’d go to rent videos?) and the premiere of the movie Road Trip (that actually happened 20 years ago yesterday). At this point, Reese and Ryan had been married about a year. They got married in 1999, three months after the premiere of Cruel Intentions and two years after they met and started dating. For some reason it always sticks in my mind what he said about shooting the scene in Cruel Intentions where Sebastian breaks up with Annette, describing how it was so hard for him to be mean to her, he went and threw up afterwards. 


In May 2000, Reese and Ryan were already parents. Their daughter Ava was born a few months prior in September 1999. It would still be another year before Legally Blonde came out and made her a big time Movie Star. They’re currently working on a third Legally Blonde movie. 

This moment in Gossip Nostalgia was brought to you by the time Reese and Ryan presented together at the Oscars in 2002. If you haven’t seen this in a while, watch up to when they open the envelope and announce the winner – because he says something that, looking back, well, everything looks a little different now, right?