Choosing the songs that define you is a tricky business to say the least, especially when the power of song has provided an ongoing soundtrack to your life. “When you’re as avid a music consumer as musical artists are, trying to pin down Nine Songs is difficult,” Darren Criss laughs. So much so, his final choices only really crystallise as our conversation draws to its close. “It’s hard for me not to see the value and joy in literally everything,” he explains. “The curse of the creative person is that your ideas and your interests always move way faster than your body can execute.”

Criss is a creative par excellence. As well as his Emmy and Golden Globe winning performance in The Assassination of Gianni Versace, where he played serial killer Andrew Cunanan, to his upcoming role in Muppets Haunted Mansion Halloween special as The Caretaker, he’s also a prolific musician. Criss enjoyed a decadent musical consumption since childhood, so “this was a bit of an archaeological dig,” he admits. As such, everything from jazz standards, to 808s, punk rock, ‘90s teen pop, and musical numbers are excavated in the course of our extemporaneous journey through the music he loves.

Equally on his mind is how to go about approaching the task of creating his Nine Songs, full stop. “The interesting social experiment is: Are my answers going to be songs that actually shaped my life and were formative to me as an artist? Are they songs that were formative to me as a human being? Or am I picking songs that I think represent who I am to people that do not know me? All three of those things aren’t necessarily the same thing.”

He reaches a conclusion of sorts. “For the purposes of making some kind of decision, I’m gonna lean less into trying to look cool to your very cool readership, and more into the literal, ‘What made me think about music in a different way? And hit me in a very emotional way?’ I think that’s probably the healthiest route.”

Embracing the accessibility that characterises Criss’ picks - or at times the initial touchpoints that led him to them - are something he vacillates over during our chat. “I’ve seen a lot of other people’s Nine Songs and they’re super cool. It’s like Leonard Cohen B-sides and old opera records and stuff. I’m gonna be pretty honest with the pop culture zeitgeist of how I grew up but explain why there is so much value in those moments.” His contemplation continues into the next day, Criss’s publicist passes on his regrets at being tentative to admit how he encountered one of his song choices via the Shrek soundtrack.

A yearning to reinterpret accessibility and the value attached to it drives Criss, however. He tells me that a festival performance that applied the anarchic verve of punk rock to a more refined Great American Songbook number remoulded his perception of music entirely. His love of the fusion of these two genres in particular symbolises the salient musical backdrops of his childhood - the guitar bands he played in with friends, and his musical theatre endeavours that led him to Broadway and multiple Ryan Murphy juggernauts, including his breakthrough playing Blaine Anderson in Glee.

Criss employs these contrasting musical lexicons, and other areas in between, on Masquerade, his new EP. Comprising five stand-alone “character-driven” singles, it sees Criss donning different musical personas. “I’m leaning into people that might know me as an actor,” he explains. “Because if actors can do Shakespeare, romantic comedy, and then do a horror movie and wear a prosthetic nose and a wig, I didn’t understand why I couldn’t just do that with music.” The song “walk of shame” draws on jazz-standard chords interlaced with hip-hop production, “i can’t dance” looks to new-wave, and “for a night like this” is the product of Criss’ goal to create the ultimate end-of-the-night crowd-pleaser for a new-year bash, wedding or bar mitzvah. “This is all of the parts of me as a lifelong fan of these genres, trying my hand at servicing the pieces of them that I love.”

“I really love all styles of music and understanding what makes them unique and special and what makes them really pop. There are so many things that really make things sing - for lack of a better verb - and I like acknowledging those things and celebrating those things.”

“So, let’s begin. I have runners up and shit, and I have artists, I don’t just have the songs, so we might have to pick them as we go.”

“Part of Your World” by Jodi Benson

“When people read this, they’ll go ‘That’s cute, he likes Disney songs’, but it’s more profound than that. Some of the most formative pieces of music to hit me at a very early age would have been any of the songs that were coming from ‘The Disney renaissance.’ The early-mid ‘90s explosion of The Little Mermaid, Aladdin and Beauty and The Beast.

"One of the through lines between the three of those musicals was Howard Ashman, who is one of my all-time heroes. Dramaturg, songwriter - he really was the voice behind what made those songs great. I have always loved Howard’s lyrical sensibility and also Alan Menken, his partner who wrote these songs with him. There was a musical structure to a lot of the songs which I would unconsciously pick up in my own songwriting, not just musically, but the idea that not only did somebody make these songs, but they wrote them for a story.

“There’s a clip of Howard Ashman vocal directing Jodi Benson, who was the original voice of Ariel. It’s a wonderful example of his genius, where not only was he songwriting but he was storytelling in the way he would tell her how to perform it, and you can really see the song coming to life in that clip. That’s when you cross the street from ‘It’s a song’ to ‘This is an experience.’

"There are certain ingredients that are required to elevate music that goes beyond just a nice melody, a beautiful orchestration and a good voice. There are things that are required to really give a performance a characterisation, context and a vulnerability, that he architects in real-time with Jodi Benson. You see that what he’s doing is what makes the record so special, and that’s something that’s always been inspiring to me.”

“MMMBop” by Hanson

“I think my love of Hanson was because some people didn’t like it, so I was like ‘Fuck you, I like this, how do you feel about it?’ But this is difficult for me, because you know, I’m speaking to The Line of Best Fit and we’re trying to be cool! Although, do you know what’s cool? Being accessible! Writing a pop hit when you are 10 years old. Being in a band with your brothers and you’re all below the age of 15, you have a record contract where you are writing, producing and performing songs that are doing well.

“I was 10 years old when their first album Middle of Nowhere came out, and I remember reading somewhere that there were these kids that had a record. At the time, I was playing guitar and I was writing songs, but in my mind I was a kid, and that was it. I couldn’t be on the radio; you had to be a grown up to do this.

"This was the first time where I realised ‘Holy shit, kids can do stuff!’ It’s the value of seeing yourself in the media - that’s a whole other conversation to talk about - but there’s an immense value in feeling like there’s a piece of you out in the zeitgeist and doing well because it’s encouraging. You go, ‘Holy shit, maybe I can do this as well.'

“When you see children doing things, you’re ‘Wow, this is so cute and fabulous’, but then when you actually look at it you go, ‘This is miles above what most people in this age group are capable of,’ and that’s all I saw, because I was in the same age group and I was so inspired by that. This whole album was really a turning point for me, where I was like, ‘I can do this, I can do music too, because these guys can.'

“Ooh La La” by Faces

“This song really blew my mind. It became my own theme. It’s that ‘Make your heart sing’, nostalgic moment when you’re a teenager, driving in the car listening to it, playing guitar with your friends and you’re singing “I wish that I knew what I know now / When I was younger.” You’re like, ‘because I’m an adult now, I’m 15-years-old. If I only knew what I know now.’

“I was doing theatre from a young age and I was part of a young conservatory called A.C.T. in San Francisco. By way of somebody who knew somebody, I had an audition for a movie. As a kid not being near New York or Los Angeles it was really exciting, and this audition was for a film called ‘Max Fischer’, which would become the movie Rushmore, which would become one of my favourite movies of all time by the now very distinguished Wes Anderson.

“Separate from my own objective love of Wes Anderson, when this movie came out I was just around the age of getting into my own sort of identity with music, but also movies - indie movies - and trying to assert who I was. So, I see this movie Rushmore and I love it. I love the soundtrack, I love it so much, it’s one of my favourite albums ever. This song is the end sequence, and the way it made me feel - the vocals on it, I could play it on guitar and it was part of a cool movie - it really represented a lot in my life.

“And because of the acting thing, and Rushmore being great - it’s about this kid in high-school who's misunderstood but has his own agenda - everything about it was just so fucking cool to me. To this day, I cite that song as one of my favourite records of all time.”

“Recently Distressed” by Phantom Planet

“A guy that really formed the way I would sing and write songs is Alex Greenwald, the frontman of Phantom Planet. I went to see Phantom Planet because I loved Rushmore and I found out that Jason Schwartzman [who had been cast as Max Fischer] was also the drummer for a band called Phantom Planet.

"So, when I saw their name on the bill I went, but I didn't know their music. I was barely 14, but their set blew my mind. It was Rock and Roll, but I loved Alex Greenwald’s voice. I loved everything, and I would follow their career from there. I always tell people that my voice is a combination of me trying to be Alex Greenwald, Paul McCartney and Rufus Wainwright, but failing. Alex was incredibly formative for me.

“One of their biggest records was a little while after I first saw them, which was the song for The O.C., "California." That was more of an Elvis Costello thing, and they employed a lot of stuff that sounded to me like The Beatles and a lot of ‘60s mod/pop-rock. But later they would employ things from Fugazi, Radiohead and harder shit, and that eclecticism, again, only accelerated my love for Phantom Planet.

“Recently Distressed” is from their 1998 album Phantom Planet Is Missing. This was a cool rock song that employed these George [Harrison] and Paul [McCartney] background vocals and included all of the things that I loved. It was harder but melodic and employed minor 4th chords and more complicated chords than I was used to. I had grown up with power chords - which are very Gregorian - on a lot of alt. punk rock, like Green Day or Nirvana, and if Kurt Cobain was using power chords then that’s how I was playing guitar. Hearing this music was like ‘Oh, I’m using full chords, not sevenths, minor 4th chords, diminished chords’, shit that I would learn to use more and more.

“When you haven’t experienced much, anything that gives a hint towards possibility, even though it’s probably always been there, you’re like, ‘I like this, I’ve always kind of liked this, but it’s very encouraging to hear somebody else do it and it’s gonna make me reconsider my possibilities.’ That was literally the moment that my power chords turned into full barre chords.”

“Cigarettes and Chocolate Milk” by Rufus Wainwright

“I forgot the other day how I got into Rufus Wainwright, because all of this stuff I was getting into quite young. It’s like when I talk to 11-13 year olds, it’s funny to think that this was when I was really starting to build my musical identity. But then I remembered, and I didn’t want to say because I didn’t want to sound uncool, because he is such a revered artist who exists in a much cooler place than what I’m about to say.

“I loved soundtracks and I would always buy soundtracks for movies that had cool playlists. I had the Shrek soundtrack, and there’s a cover of Leonard Cohen’s seminal “Hallelujah” that Rufus does and he smashes it, and I’m like, ‘Who the fuck is Rufus Wainwright? What a beautiful voice.’ Then I saw that he was going to be at the Virgin Megastore in San Francisco one week, so I go and he’s there promoting his new album Poses. I remember I didn’t have enough money to buy the album that day, so I had him sign my sneaker and I saved that shoe.

“The first song on Poses was “Cigarettes and Chocolate Milk”, which is a very dark and reflective song about his own battles with addiction, but he’s singing it over this really beautiful, whimsical song that has a lot of really great wordplay. I always love when artists, especially lyricists, can encapsulate an idea with not exactly what they’re talking about. The song’s called “Cigarettes and Chocolate Milk”, it’s not called “Addiction”. Its talking about things that he craved and how that’s representative of other things that he’s gone through. There was a sophistication and elegance to that that I really gravitated towards, that I didn’t possess but wanted to shoot for. So when I saw him, that was a big one for me and he would also continue to influence me later in my life.

“I’ve become friends with Rufus since. I’ve performed with him and we’ve made records together, which is crazy. His songwriting was very complex and punk-rock, but he had this classic cabaret voice, the kind of voice that I don’t have. I was fascinated that there was somebody that could write this really dark material but have such elegance on top of it. He was virtuosic on the piano, which I thought was very cool because musicianship is always the thing that gets me going the most about artists.

“You know what? People say, ‘Don’t meet your heroes.' I completely disagree. Chase the living fuck out of your heroes. I’ve spent a lifetime doing so, it’s made me a better artist, and I’ve sometimes got to meet them and work with them. I’ve worked on music with Alex Greenwald of Phantom Planet. I’ve performed with Hanson. I’ve performed those Disney songs with Alan Menken at The Hollywood Bowl.

"This is all because there are people that I love who I have put on my vision board, and the things that they have done are the things that are bringing me to them. So it is nuts, but at the same time you’re like, ‘Well, what else did you think would happen?’ They did stuff that some part of me connected with, so obviously there’s a magnetic pull towards that person.

“Rufus Wainwright is one of my absolute favourite artists of all time and like I said, me trying to sing like him and failing is a big part of my own journey as an artist.”

“3x5” by John Mayer

“John Mayer’s another guy that came around when I was 15. I heard a song of his on a middle-of-the-night, singer/songwriter college radio show. This is where I used to get music. You would listen to these carefully curated playlists that you wouldn’t be able to hear anywhere else, and the host played “No Such Thing”, a new song by this young kid who had just dropped out of Berklee College of Music - John Mayer.

“I’m listening to this song and I’m like, ‘Not only is this guitar playing really interesting, but the lyrical value and everything that is going on here ticks all the boxes.' It was jazz, but it was pop. And he did something that all these other guys and girls I’ve mentioned did. They made something very unique and very accessible.

“I immediately went out to buy this album, Room For Squares, and I listened to it over and over again. It was an album that was really formative for me. "3x5” is a really beautiful song that employs a lot of chord structures and melodies that blew my fucking mind at the time, and it made me wish that I could write songs like that.

“That album was a huge turning point in the way I played the guitar, because it was the first time in my life where I would look up tabs. Up until this point in my life, if I heard a song I could play it instantly. It was like a party trick, I would get how it worked if I heard it, because most of the songs I would hear on the radio - especially those that involved a guitar - were [centred around] power chords. And now I’m hearing all of these ninth chords and thirteenths, and I’m like, ‘What the fuck is this?’ So I’d have to look up tabs.

“I think any young artist can attest to this - when you try and learn other people’s shit, it’s the best tool for educating yourself. Playing other people’s music really helps you lock in what your own style is. Trying to learn these songs - and sometimes pulling it off and sometimes not - really changed the way that my hands moved around the guitar and considered chords and voicings that I’d never really thought of.

“There’s another tie to musical theatre here, where I remember seeing Audra McDonald, who is a very venerated theatre actor, and she did a cabaret. If you’re familiar with cabaret culture, it’s more about performing the story of the songs – ‘Life is a cabaret’. She did a John Mayer song because she thought it was from a musical theatre show, and I was so tickled by this, because I was like ‘Yeah, if you really think about it, I don’t think he knows this and I don’t think his fan base even thinks about this, but there’s a number of his songs that feel very theatrical in the way that the lyrics play with each other and the way the chords move’.

"When I saw this I thought, ‘That is why I like John Mayer’, because yes, he’s an amazing guitar player, but he’s also a really strong songwriter.”

“Cabaret” by Me First and the Gimme Gimmes

“Also, around this time growing up in San Francisco, as a guitar player playing music with your buddies, the number one thing that you play is punk rock. There are different parts of the spectrum of punk rock, there's the NOFX, Swingin’ Utters, like real punk, punk. And then there’s the pop-punk thing that was happening at the same time, which was also equally influential - blink-182 and Green Day.

“Fat Mike was the frontman of NOFX. I loved NOFX, and Me First and the Gimme Gimmes were a supergroup of different members from different punk bands, of which Fat Mike was one of the main architects. They would cover songs and turn them into punk rock songs. They have an album of hits from the ‘60s, and they also have an album called Me First and the Gimme Gimmes: Are a Drag, and that record is just a tonne of musical theatre covers that are done through punk rock.

“That was completely in line with everything I loved at this time of my life but didn’t really know how to articulate. I loved punk rock but I also really loved musical theatre. Not only the performative element of it, but there was a real musicality to musical theatre that wasn’t as present in some of the other shit that was popular at the time, just harmonically, or where chords would go. There was a sophistication I loved that seemed to not exist in punk rock.

“Then hearing Fat Mike at The Warped Tour going ‘Alright, which one of you Motherfuckers loves Julie Andrews?’ and hearing a mixed bag of reactions, because people were ‘What? I was not expecting that from you, sir?’ And then they start playing “My Favourite Things”, a classic Rodgers and Hammerstein song which is very accessible, but sophisticated nonetheless. And I am just living. I’m like, ‘This has got the attitude and simplicity of punk rock, but the sophistication of a beautiful song.’

“That was the first time in my life where I went, ‘It’s just all music. All these categories and boxes are completely arbitrary.’ So I thought, ‘I can do that.' I was playing power chords in punk bands but I realised that you can take chords and make them into other rhythms and voicings and have the same song. I could take a punk song and make it jazz. I could take a jazz song and make it country. So, quite providentially, I would end up on Glee, where they took popular songs and would sometimes do their own versions.

“By that point, I had been doing this my whole life. The first time this ever became a possibility for me was seeing Me First and the Gimme Gimmes, and that way of thinking about music and genre. I’ve put that into Masquerade, and it’s all born from that moment of ‘Oh my God, nothing has to be one thing. It’s just about how you look at it.'

“Cabaret” is from a pretty famous musical that I would’ve probably heard about later in life, but I first heard that song as a punk song and then I went back and heard the original. It doesn’t matter how these things happen, the inspiration happens and then you can go from there. But Me First and The Gimme Gimmes were a huge gateway drug and I play “Cabaret” now every year at my festival. That’s why the festival is called Elsie Fest, because it covers the song.”

“Modern Nature” by Sondre Lerche

“One of the great joys of being a younger brother is that you get to inherit the music of your elders. My brother and I were both really proactive consumers of music, so we would share stuff with each other all the time. But then he would come home from college, which is like coming home from a music festival essentially, right? He was in a new time zone with new people, so he’d bring home these mix CDs that he’d made from people that he’d heard about, and he brings home this guy named Sondre Lerche.

“Hearing this guy blew my mind, because he also was using jazz chords and drawing on musical theatre. Musical theatre’s a massive category, so I can’t just say that musical theatre sounds like one thing, but when I say this, I’m referring to The American Songbook, the jazz standard songbook. “Modern Nature” was a duet that I would go on to play many times with one of my oldest musical collaborators, Charlene Kaye. When we got to college and we both found out that we loved this guy.

“There was a much more whimsical way to how he wrote these songs. And what’s crazy is that loving this guy meant that we also loved Rufus Wainwright, that we also loved these other artists. But Sondre was the first time I considered that I loved that type of music, but I didn’t know that you could be a singer/songwriter and put out music that sounded like it.

“I don’t know if ‘twee’ is the right word to use, but with “Modern Nature” there was a playfulness about it, and again, a musicality that I really gravitated towards. There is a through line - there was a sophistication that was accessible, and me trying to learn those songs did make me rethink the way that I was writing music. The structures were weird and different and I liked that.

“To this day, I find myself writing songs that I think might be difficult for people to ingest, because they’re a little too left of centre, and I realise that I’m trying to write like Sondre Lerche, or I’m unconsciously just copying him.”

“Everything Happens to Me” by Mr Hudson & The Library

“I was in an H&M in Stockholm when I was 21, and I heard this really cool groove and the lyric was “Why must I always play the clown?” It was sung with a really thick British accent, had an 808 feel on it, and lyrically it had an attitude. Who would say something that sounds so like you’re in a Gilbert & Sullivan musical, but it feels hard? It was cool.

“I went home and looked this up and it was off the record A Tale of Two Cities by Mr Hudson and the Library, which would really, really fuck me up. I bought the album immediately because I loved this song. I had to order it on the internet because I couldn’t find it. It was doing well in England and he was on the festival circuit in the early-mid 2000s, but the first song on the album was a musical theatre cover with 808s.

“It was a pared-down, sort of a hip-hop version of “On The Street Where You Live” from My Fair Lady, and I’m like ‘No fucking way, this guy gets where my head is.’ I’d thought about punk rock musical theatre, but I never thought about 808s and 909s scoring these beautiful songs. I go down the track list and he has “Everything Happens to Me”, which is another very famous standard, and he had this really cool, what we would now call chill-hop, ‘study beats’ version of this song. I was like, ‘This is it. This guy gets that good music is good music and you can reinterpret it to offer it as a new song.’

“I would later become great friends with Mr Hudson. I got to meet him years later when I was with Columbia Records, and they said to me ‘Who do you want to meet?’ He was at the top of my list. I went to London and we’ve been friends ever since and have created all kinds of music together.

“He told me a story where Tyler the Creator went up to him once at Coachella and said, ‘Oh man, “Everything Happens To Me”, that’s like my song.’ We both wondered if Tyler the Creator knew that it was a Chet Baker cover. And we were thinking how cool it is that you can offer these songs to a new audience through a different lens. Tyler’s a smart guy, he’s very cultured, and I’m sure he did know. But it’s more the idea that if someone experienced this song and didn’t know that it was a cover, and this is like the first time they ever get to experience it.

“Mr Hudson would go on to do his own thing with Kanye and was on 808s & Heartbreak and has had his own career. I think “Supernova” was a hit in the UK, it didn’t really cross over here to The States, but before that moment for him, that Mr Hudson and The Library album changed my life. People use that phrase willy-nilly, but this literally was a turning point in my life. It all had to do with the same thing that happened with these other songs, where I saw someone do what I always wanted to do but didn’t really know how to pull off. Where he had this fusing of old songs delivered through a contemporary lens, but also laced it with his own original material that also employed the things that made that old songwriting interesting.

“It’s like changing the font of a great essay but finding the font and figuring out that that font is its own art form. He really displayed that marvellously on this.”

The Masquerade EP is out now