Heidecker has, of course, made a name for himself with a branch of comedy he and longtime partner Eric Wareheim can justifiably claim to be unlike anything else out there. It’s quirky and self-conscious to an uncomfortable extreme, punchline-free, and the joke is often that you either get it… or you don’t. They were doing dank memes as sketch comedy before dank memes were even a thing.

Over the course of several records - and pivotally 2019’s What the Brokenhearted Do… and Fear of Death, released a year later – Heidecker’s earned his musical credentials too. A series of choice collaborations – among them Jonathan Rado (Foxygen), Kurt Vile and Weyes Blood’s Natalie Mering – show the reverence he’s held in by the indie world.

Tim and Eric were crossing paths with the alternative scene long before Heidecker began his journey from making parody songs to crafting bona fide albums that side comfortably next to those of his heroes. Musically, he’s in a place that’s not too dissimilar to the likes of Harry Nilsson, Warren Zevon, Father John Misty and Randy Newman. Heidecker's music - like theirs - is a very American product, informed in parts by storytelling, hyperbole, and (sometimes grotesque) satire.

Heidecker’s new record High School is released next week via Matthew E White’s Spacebomb label and finds him collaborating with the likes of Mac DeMarco as he revisits his teenage years with new insight and perspective. DeMarco came on board when Jonathan Rado’s schedule couldn’t align with with Heidecker’s, and former collaborator Drew Erickson suggested DeMarco could help. “It started with him letting us use his studio – which is basically a guest-house/garage situation,” Heidecker explains. “And then he jumped in and started playing parts on it and engineering and making it with us. It was just the three of us, song by song, building the tracks. And it was perfect, he had all the right gear and the right attitude. He played a lot of lead guitar stuff, and it's just so nice and pretty and appropriate.”

He tours High School from early July - his longest stretch on the road – kicking off with a week of sold out warm-up shows at the Elysian Theatre in Los Angeles, and ending in late August with five sold-out nights at the Bell House in Brooklyn. “I do a stand-up set as my bad stand up character. And then I take a little break and come back with the band and we play the music,” Heidecker tells me. “I'm not like Robert Smith up there, you know, with the hair in front of my face. I'm myself and I make jokes and I'm self depreciating… but when I launch into a fairly serious song, there's no laughs and they're engaged. And that's my job as a performer: to make the audience react the right way.”

“Bobby Jean” by Bruce Springsteen

"The Born in the USA record – I'll say tape more than record – was so ubiquitous at a certain pivotal moment – you know, 8 or 9 years old – it was everywhere. It was really an adult record and felt very important and somehow very holy. The 'Glory Days' video was on all the time and the vision of him playing Shea Stadium was so ingrained in my early memory.

"'Bobbie Jean' was a B-side track that I probably didn't give much attention to, but only recently, over lockdown listening to his live compilation from that era – the 75 to 86 era – that one just knocked me out. Hearing it fresh, it's such an underrated, beautiful, sad song. It’s a beautiful mix of production and meaningful songwriting and pure emotion.

"I could have put twenty Bruce Springsteen songs in this list. His energy and his voice, the consistency of his career and the kind of values he seems to have are all just very inspiring."

“You Play Glockenspiel, I'll Play Drums…” by The Beautiful South

I guess the story here is that in early high school, my cousin who's my age and I was really close to had a sister - my other cousin – and she was into cool music and was kind of a punk type person, a Brit Pop aficionado and had good shit in her collection.

"I can only assume that the record this is on 0898 was in her collection. Maybe one of their songs played on that MTV show 120 Minutes too. But we were into them and the Stone Roses and this other band called Jellyfish – these bands where there was a sonic lineage to the 60s, to experimental Beatlesque pop.

"It was a record that we all loved – me and my cousin and a couple of our friends – we listened to it all the time and then we grew out of it. I just recently went back and the whole record is great. I picked that one because it’s cool, it’s got a very hip synth thing going on but it's very dark. I don't even know what he's talking about when he’s saying "You play glockenspiel, I’ll play drums,” you know? But it appeals to me, it speaks to me in some way."

“Silence Kid” by Pavement

"I have a very distinct memory of being in a band in high school and I was pretty ingrained in the classic rock cannon. I was not very into what was very popular in my crowd – which was hardcore, emo and punk. As you can see from this list, I'm such a melody guy, I love pretty melodies and harmonies and catchy pop music. Most of all the hardcore stuff didn't have any of that and I found it so boring and exhausting to listen to.

"I think the drummer in my band had Crooked Rain, Crooked Rain but I didn't know anything about them, I didn't know any of their stuff. And that line “Hand me the drum stick / Snare kick”... it was like these guys were for me right away. It reminded me of the Rolling Stones in some way – that Exile on Main Street energy – or the Velvet Underground. It was cool and funny and ironic and detached and it rocked. And I dug them right away. That album is full of hits, like just really funny, fun, catchy poppy stuff, you know? I became an immediate fan.

"I think there's a lot of stuff that I hear that I probably don't return to ever but I'm always friends with cooler people than me, and they usually know the good stuff. But what was cool about like, Pavement, at the time, was the Matador brand became a signpost….if you like this band, you'll probably like that band.

"I never pay attention to his words or stories so much – its just that his lyrics sound great and they conjure memories and ideas…except of course where he’s being literal – ”out on tour with the Smashing Pumpkins.” That felt cool too! These guys are dissing on the Smashing Pumpkins? That seems kind of dangerous!"

"Know Your Onion!" by The Shins

"This is a fun memory I have: I was working in New York after college at a desk job. I really didn't enjoy it, I was a little bit lost in life and trying to figure out what I was going to do. I was incredibly bored. It was 2003 or 2002 and so listening to music on the internet wasn't really anything you did. I think the iPod had just come out, but you still had to burn your CDs, there was no Spotify, but finding music online wasn't done very much.

"I don't know why – because I've never really done this – but I went on Sub Pop’s website and there was a Shins EP that you could stream through a QuickTime Player or a Real Player or something. This song was on and right away it was so exciting and fun and catchy! It didn't sound really like anything else. Even now I go: 'What is this even? What are their references? What does this even sound like?' I think also streaming there was the other song “New Slang”, before it was sort of co-opted by that movie. I couldn't believe how great that song was too.

"I think it was those two songs that I became really enamoured with. And then shortly after, their first album got a bunch of great press and they did a show in Hoboken. And Eric and I – before we really doing much – got to show videos before their performance, and got to meet them. The day that they were playing, they were on the cover of The Art Section of The New York Times. And I was excited because I knew who they were and I had gotten gotten in early on them. But it's just a cool ass sounding track, you know?"

“Love Gets Dangerous” by Billy Bragg

"One of my uncles is the cool uncle, my uncle Brian. They lived outside of New York, he was a big music fan and tried to keep up with what was going on by listening to Public Radio and college radio – another great way to learn about music. He had a Billy Bragg tape that he played for me; again, somebody I'd never heard of and wasn't aware of.

"I'm an Anglophile though and I love British stuff; of course I’m a Beatles freak too and I love the language and the accent – it’s all very charming. And Billy Bragg had it all, it felt so unique to have the electric guitar and folk singer sound. I don't know if anyone had really done that before or after, not that I'm aware of. But that Back To Basics record which I guess was like a collection of singles – it’s an amazing compilation of great songs, ever single one is immediately really catchy.

"When I got hip to this record, he’d just come out with another one called Don’t Try This At Home, which was much more produced – I think Peter Buck from R.E.M. had worked on it with him. His sound certainly wasn't a hit here and I don't know if it would appear on a lot of people's lists, but 'Love Gets Dangerous' sounds really cool – it’s got this cool phaser or flanger on it and the vocals are double tracked. It’s so full sounding and yet it’s just a guitar and a voice!"

“Passionate Kisses” by Lucinda Williams

"Right after college, I got a job in Philadelphia at this creperie that had just started and was run by this gay couple Jim and David. It was their first restaurant and I got the job as it opened. Jim played music all day long and had great music taste, and he loved Lucinda Williams. And this record – which I think is her first record – and Car Wheels on A Gravel Road were in heavy rotation.

"I heard those records every day. I didn't know anything about her – I wasn't a big country music fan at the time – but I can just smell the crepes when I hear this song. It’s an all-timer, the song and a lot of the songs on both of those records. Great lyrics. Great sounds. Great singer."

“A Wedding In Cherokee County” by Randy Newman

"Randy Newman said that he had started this song because he was asked to write the Albanian national anthem. It obviously doesn't go anywhere there, but melodically or musically, that's where it began.

"I was aware of Randy Newman as a kid and knew about his scoring work and some of his novelty songs like 'Short People'. And about 10 or 15 years ago, I was randomly recommended this memoir by E from The Eels. I wasn't a fan or anything, I knew them and I liked his music but I never would normally think to read his memoir, but somebody said it was really good. In the book he talks about Good Old Boys and how he became obsessed with it and it became something he listened to over and over again. And, you know, that's something you make a note of. And then I just followed the same path he went down and Randy Newman became really important. I became pretty obsessed with that record, Sail Away and a couple of the other ones.

"For me as a songwriter, I was sort of struggling, because I still really loved music, but I was so entrenched in the Tim and Eric comedy world. I’d been making sort-of satirical music and some parody records, and I didn't know how to make genuine music without being funny or I didn't know how to not be funny on it.

"And then Randy Newman comes along and shows me that you can be both. You can write pretty music, you can write sad music, you can be funny. And you can do all that in the same song if you wanted to. So it expanded in my mind what you could do with music as a writer and be funny and sad together, just like salted caramel or something! It expanded my own idea of how I could make music."

“Pure Comedy” by Father John Misty

"I'd written this song about Donald Trump's private pilot that’s very, very Randy Newman-y dark comedy… a black comedy idea of Trump’s pilot being a kamikaze pilot and crashing the plane before he can do any more damage. I put it out on my Bandcamp and Josh Tillman covered it, which was a very moving experience for me to hear him sing one of my songs because of his powerful voice.

"I didn't know him at all, I'd never met him, but I was a fan and we got in touch and had dinner. We struck up a little friendship there with common interests, it was right after the election and we both kvetched about our fears and anxieties about what was coming our way and what was happening to our country, and what was going to happen.

"He told me that he’d been a busboy at a restaurant in Seattle, when Eric and I were doing one of our earlier tours. So he was watching me do my thing before he was doing his thing, which was kind of neat. And he sent me his new record at the time and this was the first song. The first three minutes of that song just knocked me out, it really made me look again at my own songwriting and made me want to do a song like that or tell a story like that. When I was doing Fear of Death, I think it influenced me there with the song “Oh, How We Drift Away” that Natalie Mering (Weyes Blood) wrote the music for. I was really interested in writing a big song – a song about a big thing, about a view of history or a view of us as people through the aeons – a maximalist style song.

"'Pure Comedy' is just a bold ass, brave song to write and to start your record with. It's really clever and emotional. It’s certainly not a radio friendly song or anything like that – it’s headphone song – but I think those are often my favourite songs."

“The Ballad of El Goodo” by Big Star

"I have this great memory in college of a girl that I was nuts for. Nothing ever happened, but we were friends and she gave me this tape – it was both Big Star records, one on each side. It was such gold and again, pre-internet, I couldn’t tell you anything about who this band was except what I’d read about them in some Rolling Stone interview with R.E.M., where they said they were an inspiration for them.

"I picked this song because, jeez, it’s just a beautiful classic: melancholy, sad, poppy. Guitars like you've never really heard before, except maybe on Revolver. There's certainly a Beatlesque kind of Stratocaster sound going on.

"Watching the 2012 documentary about them, and hearing them for years on good sound systems, some of the myth gets dispelled a little bit – but there's something about that tape that works; it’s kind of compressed, it doesn't sound so great. It was a big, big inspiration for me and a very evocative sounding record – it's another one where you can smell the smells of the year you heard it first, when you listen each time."

High School is released on 24 June via Spacebomb Records