In 2019, Sara Bareilles accomplished what she had previously thought of as a career "impossibility": she headlined the Hollywood Bowl on a chilly November night, with her name atop the vaunted Los Angeles venue's marquee for the very first time. She never could have imagined that the next time she would set foot on the same stage, it would be in front of 17,000-plus empty seats amid a global pandemic.

But even though the Grammy-winning singer-songwriter couldn't bring her fans back to the Bowl just yet, she has two different ways to bring the Bowl to her fans: First, on Friday at 7 p.m. ET, Bareilles is hosting a livestream concert from the venue on her YouTube page, and on May 21, she'll release Amidst the Chaos: Live at the Hollywood Bowl, a 21-track project recorded at that November 2019 show.

"To imbue this event with all of the context and the experience of what last year meant, and the impossibility of being in a space like that, it just was so layered," Bareilles tells Billboard of returning to the empty Hollywood Bowl last month to record Friday's stream, which is promoting the live album as well as her new Girls5eva series about a reuniting '90s girl group, streaming now on Peacock. "It was so special and it felt really reverent to share that space and to share it with a very small amount of people."

And now the intimate show -- which includes Bareilles' full band performing an abbreviated set of Amidst the Chaos Tour songs, plus a hilarious performance with her Girls5eva bandmates Renée Elise Goldsberry, Busy Philipps and Paula Pell -- will be shared with a much bigger crowd.

Billboard was on site at the Hollywood Bowl for the recording, and we caught up with Bareilles after to discuss the emotions she felt at the initial 2019 show, the new livestream taping and why making Girls5eva amid the COVID-19 pandemic was so cathartic.

First of all, thanks so much for inviting us to a concert. What was it like for you to be back onstage and back at the Hollywood Bowl?

It was wild to be in that place empty, and it was hopeful and it was nostalgic. I was having so many feelings.

What did that first headlining show at the Bowl mean for you back in November 2019?

It was so many things. First and foremost, that place is a little bit like going to church. It's so majestic and where it's nestled and my history with Los Angeles, just what that venue meant to me as a young artist and always kind of dreaming of the possibility -- or what felt like an impossibility -- of playing the Hollywood Bowl. And then having that moment come at the end of 2019 when everyone in my world imagined that we would release this live record last year.

So now, to imbue this event with all of the context and the experience of what last year meant, and the impossibility of being in a space like that, it just was so layered. It was so special and it felt really reverent to share that space and to share it with a very small amount of people. I was a little overwhelmed. As always, it was a mad dash. You're trying to do 10 million things in a short amount of time and can't do anything with the lights until the sun goes down, and it's like "Hurry up! We have to do the show!" It was chaotic and delightful and crazy and hard and wonderful -- just like life. It was all of the things.

How bizarre was it to look out and have all those empty boxes and barely any people?

It really does bring home the power of the audience. Like, you can stand onstage in a majestic place, in a cathedral of music, and it doesn't mean the same thing without the people there to receive it. I was really struck by that, because we've all felt so isolated and we have this imagining of community because we're all having to do it from far apart. But to really be in a space that is built to support people coming together and having the people not be there, it was kind of stark.

But also, where we are in the course of this virus and the healing of the country, it did feel really hopeful to know, in a few months, there will be people here again. Maybe in a few weeks -- I don't know what the goal or exact plan is. We're not that far away from the next iteration of what our lives will look like.

Having gone to school in L.A., did the Hollywood Bowl hold some extra meaning for you?

As a brand-new UCLA student, the very first concert I ever saw in Los Angeles was at the Hollywood Bowl. My roommate and I went to see Faith Hill and Deana Carter and we sat in the very, very back, and I will never forget it. I was experiencing that venue in my new city of Los Angeles and just all of the expansive feelings that it carries with it. The Bowl in and of itself just has a warmth to it and the environment of it has such a warmth to it. So that will forever be imprinted as my first musical experience in Los Angeles.

To come full-circle and actually get to step onstage and to be onstage there -- also because I'd had little tastes of being onstage there; I was there as the Little Mermaid [in a live musical production], and I was there doing a show with Katy Perry -- but to get to be the headliner, it felt like a real milestone moment. We all have those things that we look to the future in our careers or things we hope to achieve someday, and they kind of live as these lofty goals, and that was really one of them. So I will never forget that night.

And it was so f---ing cold! [Laughs] It felt like the universe sort of helping me not take myself too serious. Because I was legit just f---ing freezing.

Did you decide ahead of time that you wanted to record that show for a live album, or do you record every show and it was decided after?

I knew that that night was going to mean a lot to me for a lot of reasons, so I knew we wanted to record it. And then that tour, the Amidst the Chaos Tour, meant so much to me as an artist as well, so I wanted people to get to experience our arrangements of those songs for that tour in particular. But everything got cut short. There was every possibility that we were going to have a European leg of that tour and bring it out again. There was a lot of talk about that, and then of course 2020 was what it was. I think all of that just made this iteration of the music more precious to me. And I felt even more determined to get that out to the fans.

Did you have some favorite live albums or live recordings growing up?

I was a big Counting Crows fan -- still am -- and they had a live record from Amsterdam [New Amsterdam: Live at Heineken Music Hall February 4–6, 2003], and that was one of my go-tos. I just thought they did such a beautiful job with that record. Bill Withers, Live at Carnegie Hall is kind of one of the ultimate albums for me. Aretha live anywhere is like just, OK, we can close the conversation there. And a lot of Bob Marley. I listened to a lot of Bob Marley growing up, and those live recordings are pretty special as well.

A lot is made of the legendary acoustics at the Bowl. What does that feel like as an artist from the stage -- both with and without a crowd?

The part of the live experience that I love the most is the sound of the audience. So it was an interesting thing. It felt like an element was missing. I have in-ear monitors, like so many artists, and lots of times I will perform with one of them out, because I just like hearing the audience sing along, I like hearing them chatter, I like talking to them and having a conversation with the audience throughout the show. So for me, I was kind of missing that element. But the acoustics are incredible there. It's just a really special space designed exactly for that, of course.

How did the livestream taping at the Bowl come about? Was it just for the live album or for the TV show, or a mixture of everything?

The idea came from Kevin Beisler, my manager, and I don't know if that idea was from him and Brandon Creed [at Full Stop], who I was working with at the time, but they had shared this idea and I loved it, so we've been really focused on trying to get it together. I just felt like it was a perfect moment to share my enthusiasm for Girls5eva, and the timing of all of it just felt so serendipitous.

This was a mad dash and a huge scramble to make this all come together. And Epic Records, my label, was absolutely incredible, some of my very close team members, my agent. Pete Giberga, who's been working with me as a consultant, he's the A&R guy who signed me to my deal and still works with me. My internal team was working so hard to make this happen. And Peacock was a wonderful partner and helped get this off the ground and brought the girls in, so we got to have that really fun "what the f--- are we doing?" moment while singing a song from the show. [Laughs] So they were hilarious and wonderful, as they always are.

You said onstage that Tina Fey called you up to be involved in Girls5eva. When did you get that call and how did the process work as a songwriter and as a castmember?

I got the call, I want to say it was maybe June inside the lockdown. I, like many people, was having a really hard time. I was having a real, real hard time, emotionally and mentally and just how to get through this time. And Tina called and I had a Zoom meeting with her, and I felt like I was in a dream or something. I felt like she was pitching me a literal fantasy. [Laughs] Like, "You want to do this fun show that's like comedy but music and about women and they're reclaiming their voice and you can work with all these incredible people?" And I'm like, "Are you f---ing for real?" I actually remember saying, "Are you sure? Because I've never done this before. Did you get the wrong number here?" But she had seen me in Waitress [on Broadway]. And they called me, and it was an immediate yes. I was like, "Yes, of course. I'm terrified, but of course I'm going to do this."

And it was such a beautiful decision. I went through the loss of a very close friend last year, and I started filming this right after he had passed. And it was so cathartic to go into that healing, loving, hilarious space with all of these wonderful people. And Tina and [executive producer/composer] Jeff [Richmond] and Meredith Scardino, the creator/showrunner, were all very inviting of me. It was a low-pressure invite to get as involved as I wanted to be with the music. Jeff Richmond has just been a tremendous partner. He's just brilliant. He's like, "You want to jump in? You want to write the song for the finale? Or you want to help shape these ideas that come up so quick?" You know, it's a lot of high jokes per minute and high musical jokes per minute, so there's a lot to play with, and they were really inviting, so it was really, really fun and very spontaneous.

And now the intimate show -- which includes Bareilles' full band performing an abbreviated set of Amidst the Chaos Tour songs, plus a hilarious performance with her Girls5eva bandmates Renée Elise Goldsberry, Busy Philipps and Paula Pell -- will be shared with a much bigger crowd.

Billboard was on site at the Hollywood Bowl for the recording, and we caught up with Bareilles after to discuss the emotions she felt at the initial 2019 show, the new livestream taping and why making Girls5eva amid the COVID-19 pandemic was so cathartic.

First of all, thanks so much for inviting us to a concert. What was it like for you to be back onstage and back at the Hollywood Bowl?

It was wild to be in that place empty, and it was hopeful and it was nostalgic. I was having so many feelings.

What did that first headlining show at the Bowl mean for you back in November 2019?

It was so many things. First and foremost, that place is a little bit like going to church. It's so majestic and where it's nestled and my history with Los Angeles, just what that venue meant to me as a young artist and always kind of dreaming of the possibility -- or what felt like an impossibility -- of playing the Hollywood Bowl. And then having that moment come at the end of 2019 when everyone in my world imagined that we would release this live record last year.

So now, to imbue this event with all of the context and the experience of what last year meant, and the impossibility of being in a space like that, it just was so layered. It was so special and it felt really reverent to share that space and to share it with a very small amount of people. I was a little overwhelmed. As always, it was a mad dash. You're trying to do 10 million things in a short amount of time and can't do anything with the lights until the sun goes down, and it's like "Hurry up! We have to do the show!" It was chaotic and delightful and crazy and hard and wonderful -- just like life. It was all of the things.

How bizarre was it to look out and have all those empty boxes and barely any people?

It really does bring home the power of the audience. Like, you can stand onstage in a majestic place, in a cathedral of music, and it doesn't mean the same thing without the people there to receive it. I was really struck by that, because we've all felt so isolated and we have this imagining of community because we're all having to do it from far apart. But to really be in a space that is built to support people coming together and having the people not be there, it was kind of stark.

But also, where we are in the course of this virus and the healing of the country, it did feel really hopeful to know, in a few months, there will be people here again. Maybe in a few weeks -- I don't know what the goal or exact plan is. We're not that far away from the next iteration of what our lives will look like.

Having gone to school in L.A., did the Hollywood Bowl hold some extra meaning for you?

As a brand-new UCLA student, the very first concert I ever saw in Los Angeles was at the Hollywood Bowl. My roommate and I went to see Faith Hill and Deana Carter and we sat in the very, very back, and I will never forget it. I was experiencing that venue in my new city of Los Angeles and just all of the expansive feelings that it carries with it. The Bowl in and of itself just has a warmth to it and the environment of it has such a warmth to it. So that will forever be imprinted as my first musical experience in Los Angeles.

To come full-circle and actually get to step onstage and to be onstage there -- also because I'd had little tastes of being onstage there; I was there as the Little Mermaid [in a live musical production], and I was there doing a show with Katy Perry -- but to get to be the headliner, it felt like a real milestone moment. We all have those things that we look to the future in our careers or things we hope to achieve someday, and they kind of live as these lofty goals, and that was really one of them. So I will never forget that night.

And it was so f---ing cold! [Laughs] It felt like the universe sort of helping me not take myself too serious. Because I was legit just f---ing freezing.

Did you decide ahead of time that you wanted to record that show for a live album, or do you record every show and it was decided after?

I knew that that night was going to mean a lot to me for a lot of reasons, so I knew we wanted to record it. And then that tour, the Amidst the Chaos Tour, meant so much to me as an artist as well, so I wanted people to get to experience our arrangements of those songs for that tour in particular. But everything got cut short. There was every possibility that we were going to have a European leg of that tour and bring it out again. There was a lot of talk about that, and then of course 2020 was what it was. I think all of that just made this iteration of the music more precious to me. And I felt even more determined to get that out to the fans.

Did you have some favorite live albums or live recordings growing up?

I was a big Counting Crows fan -- still am -- and they had a live record from Amsterdam [New Amsterdam: Live at Heineken Music Hall February 4–6, 2003], and that was one of my go-tos. I just thought they did such a beautiful job with that record. Bill Withers, Live at Carnegie Hall is kind of one of the ultimate albums for me. Aretha live anywhere is like just, OK, we can close the conversation there. And a lot of Bob Marley. I listened to a lot of Bob Marley growing up, and those live recordings are pretty special as well.

A lot is made of the legendary acoustics at the Bowl. What does that feel like as an artist from the stage -- both with and without a crowd?

The part of the live experience that I love the most is the sound of the audience. So it was an interesting thing. It felt like an element was missing. I have in-ear monitors, like so many artists, and lots of times I will perform with one of them out, because I just like hearing the audience sing along, I like hearing them chatter, I like talking to them and having a conversation with the audience throughout the show. So for me, I was kind of missing that element. But the acoustics are incredible there. It's just a really special space designed exactly for that, of course.

How did the livestream taping at the Bowl come about? Was it just for the live album or for the TV show, or a mixture of everything?

The idea came from Kevin Beisler, my manager, and I don't know if that idea was from him and Brandon Creed [at Full Stop], who I was working with at the time, but they had shared this idea and I loved it, so we've been really focused on trying to get it together. I just felt like it was a perfect moment to share my enthusiasm for Girls5eva, and the timing of all of it just felt so serendipitous.

This was a mad dash and a huge scramble to make this all come together. And Epic Records, my label, was absolutely incredible, some of my very close team members, my agent. Pete Giberga, who's been working with me as a consultant, he's the A&R guy who signed me to my deal and still works with me. My internal team was working so hard to make this happen. And Peacock was a wonderful partner and helped get this off the ground and brought the girls in, so we got to have that really fun "what the f--- are we doing?" moment while singing a song from the show. [Laughs] So they were hilarious and wonderful, as they always are.

You said onstage that Tina Fey called you up to be involved in Girls5eva. When did you get that call and how did the process work as a songwriter and as a castmember?

I got the call, I want to say it was maybe June inside the lockdown. I, like many people, was having a really hard time. I was having a real, real hard time, emotionally and mentally and just how to get through this time. And Tina called and I had a Zoom meeting with her, and I felt like I was in a dream or something. I felt like she was pitching me a literal fantasy. [Laughs] Like, "You want to do this fun show that's like comedy but music and about women and they're reclaiming their voice and you can work with all these incredible people?" And I'm like, "Are you f---ing for real?" I actually remember saying, "Are you sure? Because I've never done this before. Did you get the wrong number here?" But she had seen me in Waitress [on Broadway]. And they called me, and it was an immediate yes. I was like, "Yes, of course. I'm terrified, but of course I'm going to do this."

And it was such a beautiful decision. I went through the loss of a very close friend last year, and I started filming this right after he had passed. And it was so cathartic to go into that healing, loving, hilarious space with all of these wonderful people. And Tina and [executive producer/composer] Jeff [Richmond] and Meredith Scardino, the creator/showrunner, were all very inviting of me. It was a low-pressure invite to get as involved as I wanted to be with the music. Jeff Richmond has just been a tremendous partner. He's just brilliant. He's like, "You want to jump in? You want to write the song for the finale? Or you want to help shape these ideas that come up so quick?" You know, it's a lot of high jokes per minute and high musical jokes per minute, so there's a lot to play with, and they were really inviting, so it was really, really fun and very spontaneous.

It was a real amalgamation, I'd say. It was a real pastiche of a lot of groups. … The people I listened to the most were probably Destiny's Child and *NSYNC -- even though it's a boy group -- and then I was a big Britney and Christina fan also. So I did a lot of that traditional pop music, I loved that a lot. But there's little bits of ABBA in there for me. You're just writing songs that feel like comfort food, like candy.

They did so much research. The wardrobe department was incredible, hair and makeup was incredible. Everybody did so much homework. And we were also making a show inside this pandemic, where there was this really beautiful undercurrent of gratitude that we even had the privilege of going to work. So even though the COVID protocol was really stringent and hard at times, there was so much patience and generosity on set because everyone was so happy to be working at all. It was really amazing.

We obviously know of both you and Renée as musicians and as singers, but what was it like for Busy and Paula to hop in and hang with you guys? Did they have musical backgrounds too that we don't know about?

I was ready for it to be, like, "Oh, is this going to be hard?" And it was like, "Byeee, no big deal." [Laughs] It was so wonderful and easy. Busy has a beautiful voice and she's super confident, as she is with everything. She has this beautiful, bubbly [presence] -- she's like champagne. So much fun to be around. And she's a beautiful singer, great voice, beautiful tone. And Paula is a musical theater nerd, so she's a total encyclopedia about early Broadway songs, she loves Broadway, and she has a beautiful voice. So we had so much fun actually really singing together and working on our blend and singing for real. So it was really nice to have the freedom of getting to play in the moment without having to over-dub or change things. We were just really singing in the room.

And what was the acting aspect like for you? Of course, you stepped into the starring role of Waitress on Broadway, so it's not brand-new, but I'm guessing it's a whole new world in TV land.

TV land was very intimidating at first, and I felt really lucky to be supported and everyone had a lot of patience for me. It was like, "OK, Sarah, don't stand in the light of someone else." [Laughs] You have to learn how to be on a TV set and eye lines and not crossing the camera. There was a lot I felt like I was learning a little bit trial by fire, but I really took the approach that I got kind of educated with in theater, which is just to listen and respond and to stay focused and present.

But I felt like I was learning so much from these women every day. They're so playful, they're so inventive, they're so free. So I'm hopeful that there will be a progression in the development even throughout these episodes, that you're seeing my comfortability increasing. But I related to the character a lot. She's a little bit of an anxious mess, but she has a lot of heart. She's kind of doing her best, but f---ing up all the time. I'm like, "Yeah! That's me! I can totally do this!" [Laughs] It was a really healing, wonderful experience to be a part of.

Thank you again for my first live music experience in forever, and I'm really looking forward to hearing the live album later this month. May is a really big Sara month, clearly.

It's a really big Sara month! They're thinking about changing the name of the month, but I've been telling them: Don't do that, it's tacky. [Laughs]

Amidst the Chaos: Live at the Hollywood Bowl full tracklist:

Orpheus / Fire
Poetry by Dead Men
Eyes on You
I Choose You
Love Song
Armor
If I Can't Have You (feat. Emily King)
Miss Simone
Someone Who Loves Me (feat. The Milk Carton Kids)
A Safe Place to Land
You Matter to Me (feat. Solomon Dorsey)
Bad Idea (feat. Butterfly Boucher)
She Used to Be Mine
Uncharted
No Such Thing / Satellite Call
Let The Rain
King of Anything
Brave
Orpheus (feat. T Bone Burnett)
Gravity (feat. Rob Moose)
Saint Honesty