Winona Ryder is out promoting Beetlejuice Beetlejuice, and in an interview with Esquire she mentions meeting with Michel Gondry to discuss the role of Clementine in Eternal Sunshine. Of course we know this eventually went to Kate Winslet.

When she did find a script she liked, her celebrity was such that it, too, began to limit her opportunities.

“There was baggage,” she says. The obsessive interest in her love life. The hoopla that surrounded her. “Trying to convince someone to ignore the noise around me was tough. I saw it in their eyes. I lost a lot of parts because of that.”

She remembers a meeting with the director Michel Gondry, who was casting what would become Eternal Sunshine of the Spotless Mind, from a screenplay by Charlie Kaufman. “It was such a brilliant script and we were at this little restaurant and people kept coming up to me and there was a random paparazzi guy outside, which was kind of unusual for me, but I just remember [Gondry’s] face, and trying to convince him that this isn’t normal, and I know it’s not normal.” The part went to Kate Winslet.

“I’m not in any way complaining,” she says. “But there was this whole time when I felt like I would be a distraction, as well. I got it. Certainly, in the 1990s, I became aware of that. And there was a switching-of-the-guard feeling, too. As you get older there are these new, younger actresses. It’s so drilled into you how disposable actresses can be, our shelf life. You hear it all the time.” (Source)

I can imagine her in this role. She probably would've been great, but Kate Winslet was fantastic.