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'Web Therapy': Lisa Kudrow and Rosie O'Donnell

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The stories behind how Lisa Kudrow and her team at Web Therapy, which kicks off its fourth season today, scored their guest stars this season are almost as good as the storylines that bring them to the improvised online series. (Key word: Almost, but more on that in a bit.)

Take singer Natasha Bedingfield, for instance. Without a casting director, the duties fall to Kudrow, who also stars as (unlicensed) therapist Fiona Wallace, producing partner Dan Bucatinsky (The Comeback) and writer-director Don Roos (Happy Endings). So they’ve learned to keep their eyes open for opportunities at every corner — even if those corners are behind the scenes at the Tonight Show with Jay Leno. “There was a story we had wanted to do and I ran into her at the Tonight Show,” says Kudrow, who created the series for the web with Bucatinsky and Roos in 2008. “I said, ‘Do you act?’ and she was like, ‘Oh, yeah!’ And she was available.”

Bedingfield will appear later this season playing a British palace worker who seeks Wallace’s help. “Fiona ‘understands’ that she doesn’t really need therapy. She thinks she’s probably calling as a proxy to somebody else — and that’s thrilling to her. She thinks she’s calling for Kate and William,” Kudrow says.

Also on the other end of Fiona’s web cam this season will be Rosie O’Donnell, who guests in the premiere episode (watch it here) as book publisher Maxine DeMaine; Conan O’Brien, who plays a patient (and himself!); and Minnie Driver, who dons a wig to play a former child star who wants to star in the movie adaptation of Fiona’s book. Lily Tomlin will also reprise her role as Fiona’s mother, and, as Kudrow teases, this time around, she has puppets. “These take place from within her suite at the institution,” she explains. “She’s concerned that she might have killed her roommate. It’s hilarious.”

But going into its 17-episode fourth season and still “as independent as it can be” production-wise, Kudrow says the series now finds itself dealing with a welcomed problem. “We actually have a list of people now who want to do it, and that’s pretty thrilling. Now, the only thing holding us back is that we don’t shoot enough of these to accommodate everyone who could be doing it!”

Meanwhile, Kudrow says they’re still “not certain” whether Showtime will pick up another season of the show for broadcast on the cable net, but says “it’s looking good.” (The show aired over the summer on the cabler in a half-hour format, with the episodes comprised of the webisodes and material formerly available only via mobile devices.) “All we can do is make sure it’s as good as it can be,” she says. “I think that’s a safe rule for yourself.”

Watch an exclusive behind-the-scenes clip from today’s season premiere with Rosie O’Donnell.

To kick off the season, Lisa Kudrow and Rosie O’Donnell will have a Live tweet session from 2:15-3:00 p.m. PT. Follow along: @lisakudrow and @Rosie.

Read more:

‘Romy and  Michele’: 15 Years Later

Lisa Kudrow talks’ Web Therapy’ and ‘Episodes’

TV’s craziest therapist