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Acting guru and ex-Parisian pimp — seriously — James Lipton has never had trouble attracting big names to Inside the Actors Studio, which began airing on Bravo in 1994. Lipton’s first interview was with former Actors Studio president Paul Newman; the show’s first season also featured heavy hitters like Alec Baldwin, Sally Field, Dennis Hopper, Arthur Miller, Neil Simon, and Stephen Sondheim.

Nearly 20 years later, Lipton has chatted with hundreds of boldfaced names both awe-inspiring (Meryl Streep! Morgan Freeman! ) and… occasionally less awe-inspiring (was anyone really yearning to hear J. Lo describe her craft?). And naturally, those visits have produced days’ worth of footage containing innumerable gems. So, on the eve of the show’s big 250th Episode Spectacular — which airs tonight at 7 p.m. ET and will feature repeat visitors Bradley Cooper, Robert De Niro, Christopher Walken, Barbara Walters, and, er, Jennifer Lopez again — we looked back at some of our favorite moments from episodes past.

5. Young Bradley Cooper has a question for Sean Penn (1999)

In the late ’90s, the future Hangover star — and Oscar nominee — was just a doofy-haired 20-something studying for his acting MFA. When Sean Penn stopped in to do an episode of Lipton’s show, that doofy kid was in the audience — and he didn’t miss a chance to ask one of his idols about returning to an old role in 1998’s Hurlyburly. This video should give all young thespians hope, especially since Cooper ended up starring in his very own episode of Actors Studio 12 years later.

4. Kate Winslet’s crazy Harvey Keitel story (2004)

After being asked what it was like to work with Keitel in 1999’s Holy Smoke, Winslet launched into an amazing anecdote that involves Enya, Jane Campion, and a certain celebrated actor lying on the floor and pretending to be a dying dog. Best quote: “This, I kid you not, goes on for about five tracks of Enya.”

3. Natalie Portman’s favorite swear word (2004)

What inspired that filthy rap Portman performed on SNL in 2008? Maybe it was this moment from her Actors Studio episode, when she told Lipton that her favorite curse word is an Arabic expression: “Kus emek. It means ‘your mother’s vagina.'”

2. The Simpsons cast speaks (2003)

For the full effect, you’ll want to watch the episode in its entirety. But this short clip gives a brief impression of how cool — and disconcerting — it is to see the voices of animation’s most famous family coming out of real, live people. (It’s pretty cool when the cast of Family Guy does it too.)

1. Kevin Spacey, master impressionist (2000)

A lot of actors indulge Lipton by performing impressions on the show — think Tina Fey as Sarah Palin, or Jim Carrey bringing out his James Dean. But Kevin Spacey put them all to shame, slipping into perfectly-voiced impersonations of everyone from Johnny Carson to Katharine Hepburn to Christopher Walken in the span of just six and a half minutes — with some prompting from Lipton, of course. The only one that needs a little work is his Marlon Brando, who’s a little closer to Eric Cartman than The Godfather.

Special Bonus Clip: Will Ferrell’s Lipton interviewing Alec Baldwin’s Charles Nelson Reilly on SNL (2001)

Sure, this didn’t actually happen on Inside the Actors Studio. But it’s still pretty scrumtrulescent.

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Inside the Actors Studio
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