-Our first guest tonight is an Emmy-winning talk show host
and actress you know from movies such as "A League of Their Own"
and "Sleepless in Seattle."
She stars in the new series "American Gigolo."
New episodes air Friday nights on Showtime.
Let's take a look.
-You said you talked to that guy.
-Finnegan. Kevin Finnegan. -Right.
-Yeah, I talked to him. -Okay. What did he say?
-Well, it was hard to tell what he was saying.
He was on his deathbed.
He was nearly gone, you know.
I get in there and I said, "Who hired you?
Who hired you? Who hired you? I'm talking about this case."
And I don't know what, but he started, like, mumbling stuff.
Didn't make a lot of sense. Didn't sound like words either.
But I thought maybe it would make some sense to you.
-What did he say?
-He said Keene.
-Please welcome back to the show and to her former studio,
the one, the only Rosie O'Donnell, everybody.
♪♪ [ Cheers and applause ]
♪♪
How are you? -I'm well, how are you?
-I'm great. Do you feel it?
I know the physical space is the same.
It looks so different. -It looks very different.
But coming in here you get the, like, "Whoa."
That was a quarter century ago, right?
-It was a quarter -- Yeah, I guess 20-plus years.
And you did it I guess it was about six, seven years
you did your show? -Six years.
-Yeah. Doing it live.
You were doing it live as well. That's a whole nother thing.
-And it kind of keeps you on your toes though.
-Yeah. -I didn't want some studio
executive to come and say, "I didn't really enjoy
the Dom DeLuise cooking segment.
Could you do it again?" -Right?
-And I was like, "Can't, we're live. It's out there."
-I want to ask real quick because I was lucky enough to be
onstage presenting this award to Sheryl Lee Ralph last night.
-Fantastic. -Which was really a stunning moment.
First of all, well-deserved award.
She's doing fantastic work this year on television.
-Yes. -It was scene stealing
on a night, where obviously, the best in television are there.
-You know, I've known her since she was in
the original cast of "Dreamgirls."
And on "The Flintstones," she played the adoption agency
that got the me Bamm-Bamm. -Uh-huh.
-So I've known her for a long time.
And she's a genius.
She's an amazing artist, an amazing woman.
And I was so proud of her, the way she delivered her speech.
She sang from her heart.
I don't know. I was crying at home, watching it.
-It was a really special thing to be in the room for because
you realize in the way that you've overlapped with her,
you got the sense she's been doing this for so long,
in so many different places that she had probably just
affected everybody's life in there at some place,
and they were all so proud and happy for her.
-Yeah, and to see someone
be able to really live in the moment.
Like, I don't know, when I've won an award,
I'm always sort of out of my body.
And I kind of like watch it going, "Oh, my God.
I got to say something. Try to be funny,
get to the backstage area, hold in your stomach."
I don't ever take the moment
to see somebody just live authentically
and just land there and go, "This is what I'm feeling."
-It was really cool to see. -It was beautiful, I agree.
I loved the Emmys, by the way. -I thought it was great.
-I thought they were great last night.
-Yeah, I thought they were, you know, wrong on one or two.
[ Laughter ]
I don't mean it. I don't mean it.
[ Laughter ]
-I love that, though. I love the faces when you can
see the woman or the man who doesn't win.
It's just a millisecond of, "Oh, crap."
-Yeah. [ Laughter ]
Well, that's when you go, "You really didn't deserve
because right now you're being a terrible actor."
-Exactly. Exactly. -When they're like --
-Yeah. Isn't that nice?
I was very happy for Jean Smart. -Yeah.
-That show "Hacks" is genius, and she is astonishing.
-Very similar -- someone who has been around forever
and just doing such great work.
And then all of a sudden, a couple of, you know, projects
come that everybody's watching and it felt like collectively
they all said, "Oh, Jean Smart has been amazing forever"
and she finally gets what she deserves.
-She's just been funny nonstop through her whole career.
And she's doing dramatic roles now.
And this role, I think, fits her like a glove.
-Yeah. -I just love the show.
I think it's absolutely epic. -And it's a hard thing to do
when you play a comedian because you have to be
believably funny in a way -- -Which she totally is.
-She really is. -In the stand-up part, remember
Sally Field did the stand-up show "Punchline"?
-Yes. -It's a hard thing to learn.
But because she's maybe naturally a comedian,
she killed it. -Mm-hmm.
-She killed it at the stand-up club.
Like, you're watching, going, "This is so believable."
-I just read a wonderful interview with you
in "The New Yorker" about your early stand-up days,
that you decided to do that
as a path to find your way onstage on Broadway.
-Yes. -And so what was it about
stand-up that you thought might be the first step there?
Because it does seem a little unconventional.
-Well, there was a kid in my class named Craig Minervini,
and his older brother Richie was a stand-up comic.
And he was older by like 15 years.
So came to see our senior show, where you make fun of everyone.
And I was the star of it, making fun of all the teachers.
And he said, "You should be a stand-up comic."
And I said, "I really want to be on Broadway
or a backup singer for Bette Midler."
[ Laughter ]
The fact that I can't sing
didn't really stop me from dreaming that.
-Bette Midler will take anybody. She's not a perfectionist.
-She really will, to be a Harlette.
That's what her backup singers were called.
-I remember. -That was my goal in life
and to get in a Broadway show.
So I said to him, "Richie, I don't want to do it."
And he said, "Well, come down tomorrow night."
It was a Saturday night
and all the kids from my high school were there.
And I had no material because I was 16.
And I'd say, "Oh, you know what?
Mary Lynn is dating Mitchell, and Steve doesn't know."
And the class of seniors were like,
"Oh, my God, that's so good!"
So I got like a standing ovation,
and the owner of the club, Richie, comes over to me
and says, "Rosie, why don't you come back tomorrow?"
And I thought, "Uh, it's a school night.
I don't know. It's a Sunday. My friends won't -- Okay."
I went back and I killed.
I mean, I bombed. I mean, I bombed a death
that could have been heard in other countries far away.
It was pure silence. And I walked off and he said,
"So that's pretty much the life of a comic.
You kill it one night, and you really suck the next.
And why don't you come back and be the emcee?"
-Oh, wow. -And that's how I learned to do
stand-up, by watching all those comics for so many years
and being the one to introduce them
and then sit in the club and watch them.
-That's fascinating because I bet you were both learning
how to be a comic by watching, but I bet you were also learning
host skills by being an emcee. -100%.
-Yeah. Because the host's job, certainly those stand-up nights,
is to make the room better for the people who are going
to come onstage. -Exactly.
-And I would imagine you were great at that.
-I really loved doing it because I really loved
supporting the other acts.
I really loved getting the crowd ready and not doing too much
to spoil them for the headliner or whatnot.
And then Shirley Hemphill was the headliner.
And she came in and saw me on the open-mike night before.
And she said to the club owner, Richie,
"You're going to pay her $50 a show
and she's going to open for me this weekend."
He said, "No way, we pay her 20 bucks to emcee the whole night
and we're not doing that."
And she said, "Then I'm walking."
And she literally threatened to walk out of the club.
And he had to fold.
And he hired me and I made $300 in a weekend, when you're 16.
I thought I was like Leona Helmsley.
I'm like, "Everybody --" or Oprah, "You have a car.
You have a car." You know?
-That's wonderful.
[ Applause ]
Obviously you're back in your old studio.
You got to revisit another piece of your old work.
There's a wonderful "League of Their Own" television show
right now that you guys are doing a cameo in.
-Yes. -We've talked in the past
about the film itself, which is really perfection.
-It really is. -It's so tight.
And it's so well-crafted and the performances are indelible.
Did you have any hesitation when you heard,
"Oh, they're going to make a series"?
-Well, I met Abbi Jacobson with Natasha Lyonne.
I'm friends with Natasha. We did a play together.
And she's introduced me to these 30-year-old kids
who are unbelievably gifted.
And so she brings Abbi to dinner, and Abbi says,
"I met with Penny" -- this is like 2018 --
"and she said she would be very supportive of us doing a show
that 'League of Their Own' is based on
but looks more into the sexuality
and the private lives and the racism that occurred."
And I remember thinking, "That's going to be tough, right?"
But I didn't say that to her, I said, "Well, all the support
you need, if you ever need me to play like a butchy bartender,
just call me up, you know?" [ Laughter ]
And so when the show was written she called me up, she said,
"Remember that butchy bartender?"
I said, "Yes, I do."
She said, "Will you come to Pittsburgh?"
And I walked into the set and here are all these
30-year-old women, like I was when I did it,
wearing our uniforms,
saying like the lines in the vernacular of the 1940s.
It was like I flashed back all of a sudden.
And I realized that was half my life ago.
-Yeah. -Because I'm 60.
And I was 30 when I was doing that show.
And I just looked at them and thought,
"What an amazing 30 years you guys have left."
That was the start of my career.
And this is the start of many of their careers.
And to look back at 60 and go, "My God, what you have coming up
is going to be thrilling."
-It must also be thrilling for you to notice in those 30 years,
you know, sexuality was -- you could maybe say was
some subtext in the original film.
-Not really. -Barely, right?
-Yeah. -But the fact that it gets to be
so out in the open and the focus of it now --
I mean, I think you were a huge part of the advancements
in the last 30 years but that must be
such a cool thing to see. -Thank you very much.
[ Cheers and applause ] It's overwhelming.
You know, it really is.
When I watch the show, I can't believe
that we're able to have representation.
You know, when we did the actual series,
we would meet the original members of the Peaches,
and they would be like, you know, 88
and say, "This is my roommate Betsy."
I'm like, "Oh, hi, Betsy.
Obviously you played shortstop."
She was like, "Yeah, I did."
I'm like, "Okay, and how long have you guys been roommates?"
"Oh, 52 years."
[ Laughter ]
And it's just -- Society has changed so much.
People don't realize, they say, "Why didn't Penny add that?"
Well, in 1991 when we were shooting it, nobody was out.
K.D. Lang wasn't out, right?
I mean, it was a different time.
And I couldn't really believe
where we have gone in the 30 years.
Although there's a lot more to go
and I think that representation is the first step.
And Abbi Jacobson hit it out of the park, so to speak,
in this "League of Their Own" thing. She really did.
-Yeah, she did an incredible job.
And it was really wonderful to see you in that.
It's wonderful to have you back here.
Thank you so much, Rosie. You're always welcome.
-Thank you. Great to see you. Any time.
You're always welcome. Rosie O'Donnell, everybody.
New episodes of "American Gigolo" air
Friday nights on Showtime.
We'll be right back with Kevin Smith.