In the Pose season two finale, Blanca performs Whitney Houston’s iconic rendition of the “Star Spangled Banner.” Photo: Vulture and FX

It’s tough to overstate the historic importance of music in film, what with how audiences had to rely on soundtracks in the not-so-silent, pre-talkie era to fully understand the dramatic tension or madcap hilarity of what they were seeing onscreen. Today, selecting the appropriate scores or songs to accompany everything from blockbuster movies to indie-film trailers remains an art form itself, which is why the role of music supervisor is so crucial.

On its surface, the gig seems like a dream: you get to put together a playlist, of your choosing!, which will go on to define a movie or a television show. Great taste, a good ear, a knack for sniffing out rare gems — all are components of the job. They’re far from the only requirements, though. It’s clearing the rights to use a song that often results in sleepless nights and splitting behind-the-scenes headaches. The cost of it all, the debates over artistic integrity, the eternal search for approval from higher up and higher up higher-ups — that’s the stuff of nightmares.

According to the music supervisors who spoke with Vulture, acts like the Beatles, the Rolling Stones, Madonna, and U2 are among some of the most predictably difficult artists to license. Less expected names include Richard Carpenter, Dire Straits, and ABBA. The price tag can be the dealbreaker — an extreme example is the Beatles charging $250,000 for Mad Men’s use of “Tomorrow Never Knows” — but more often than not, the hitch in the deal has to do with an artist who’s worried about how their association with a particular movie or TV show might affect their brand.

“On The Walking Dead, we were working on a scene where Rick and his team had wiped out a huge mass of walkers and to get rid of them, they wanted to set the bodies on fire,” says SuperMusicVision’s Yvette Metoyer, whose credits include Breaking Bad and Halt and Catch Fire. “For that sequence, we were interested in using a Jimi Hendrix’s ‘Crying Blue Rain,’ not one of his well-known songs, and we spoke to a representative of his estate. Initially, they were open to the idea but there was the requirement that his songs cannot be used over any violent scene, drug use, or sex. There was no wiggle room. We said, ‘Well, there isn’t violence, per se, but we do see this character setting fire to bodies of walkers.’ They weren’t even human. They said, ‘Nope. It can’t happen.’”

Situations like this require some finessing, in the form of phone calls, emails, and even hand-written letters, as has become the norm. In essence, you’ve got to beg.

“With Reservoir Dogs, I really had to fight to get ‘Stuck in the Middle With You,’” says Karyn Rachtman, who also worked on Pulp Fiction, Clueless, and Reality Bites. “Getting that in a low-budget film in a scene where somebody gets their ear cut off was really hard. I had to get on the phone with Joe Egan [from Stealers Wheel] and convince him. I said, ‘This is the best script I’ve ever read,’ and brought up ‘Singin’ in the Rain’ and how it was used in A Clockwork Orange. I guess, to my credit, I had the ability to really get people rallied around the project.”

Shifts in the entertainment industry have helped music supervisors. Before the era of prestige television, movies were seen by musicians as the superior art form, so licensing for TV was often a nonstarter. Also gone are the days when making money from licensing was seen as a “sellout” move, thanks to traditional music sales no longer paying the bills. “Iconic artists like Michael Jackson and Prince were notoriously hard to get, but then you also had bands like Arcade Fire, Arctic Monkeys or Kings of Leon that would never license 10 years ago,” says Sanaz Lavaedian of mOcean, an agency that recently did the trailer music for Avengers: Endgame and Toy Story 4. “With the music industry being leveled after streaming and MP3s, artists have realized this is is a really good way of making money besides like merch and touring.”

That doesn’t mean music supervision is easy these days. Often, the biggest contemporary hurdle is tracking down who owns the rights for certain songs. This can involve a bit of sleuthing; checking publishing records to find the contact information of people who might not have worked in decades to give their approval. When trying to clear a rap song for HBO’s Ballers, Urdang discovered that the man listed as the author of the track actually had nothing to do with its writing — he’d somehow falsified the information on the publishing records. Hip-hop in general, according to her and Metoyer, is a minefield for clearances thanks to sampling and improper crediting.

“There’s so much good music from the golden era of hip-hop that can’t be used because those samples were never cleared,” says Metoyer. “Those were young kids that were building those songs, using their parents records or whatever they bought from the store. They really hadn’t thought beyond selling a few copies to folks in their neighborhood and the potential to make money later down the line wasn’t something that was on their mind at the time. It’s probably too time-consuming and expensive to go back now and figure out the splits and ownership rights. It’s a shame.”

Vulture chatted with music supervisors who’ve worked on some of the most acclaimed movies and television series in the past three decades to hear about the toughest gigs in their careers:

Smashed (2012), a karaoke scene

Tiffany Anders: The hardest aspects of the job are definitely clearance and budget. PEN15 was interesting because it’s set in 2000 and it’s middle-school girls, so music is going to play a huge role. We did not have a lot of money on that show and it was the first and last episodes where we spent the money. We had a strategy of “the opening episode is really important because we need people to connect with this show,” so we used big songs from TLC, Mandy Moore, Lit, ’N Sync. In the last episode, because there was the school dance, we had Des’ree, K-Ci & JoJo, Big Punisher. We were really careful about how we used music. The PEN15 team were so great to work with because they understood those limitations, where it was going to be important and where we could lose stuff.

This is a pretty good story: I’ve worked with the director James Ponsoldt on a bunch on his films. His second film I worked, Smashed, was very, very low budget. There was this scene written in the script where Mary Elizabeth Winstead’s character sings karaoke. I think my budget overall for the whole movie was something like $12,000 and I said, “I don’t know how we’re going to do this. We have no money for like a recognizable song.” Then we landed on “Cruel to Be Kind” by Nick Lowe. That song’s actually co-written with Ian Gomm, who was part of that pub-rock scene in England at the time. We both love the song and it worked for the character and what she was going through at the time. It was upbeat and happy and this wasn’t a happy character.

I went to the label and the publisher. The publisher just said, “This is just too low of a fee. We can’t do this.” So I made James write a letter asking for it, and then I included a story in the letter. So, my mother lived in England when she was pregnant with me. She worked at this pub in London, the Hope and Anchor, and I wrote in the letter, “This song is also important for me because when I was a fetus, my mother worked at the pub where you used to play all the time, so I heard your music when I was in utero. Please, please let us have the song.” And they let us have it. I think we got it for like something really, really low, like $2,500, but with a backend deal so that if the movie did well, he would get a certain amount.

James always brings that up. “Remember when you wrote to Nick Lowe and said, ‘I was in my mom’s stomach when you were playing at the Hope and Anchor and we have to have this song’?” All the things that you end up resorting to, to get somebody to give a song to you …

Pose, season two (2019), a national anthem sung by Whitney Houston

Amanda Krieg Thomas: We were chasing him. I tried every email, every phone number we could find for his individual publishing company. A member of my team, my music coordinator, was Facebook friends with someone who knew him, so he reached out to this one person he hadn’t talked to in many years. My coordinator’s friend then connected us to a close friend of the arranger, who then connected us to the arranger, who was in the woods of Washington teaching a workshop. Meanwhile, his manager was on safari, and we found him through another mutual friend on Facebook and used WhatsApp to talk to him in Africa.

In situations like that, we send them a form with all the necessary information, the requested rights, a suggested fee. When it’s down to the wire, especially if it’s a song that we know will stay in the final cut, the key information is, “We need you to confirm that you actually do control this and that you approve the use.” Once we finally got a hold of everybody, they were very excited to be a part of it. So that part was easy. We finally got it cleared the night before the scene was shot.

In the 11th hour like that, you just try every possible connection and hope and hope that one of them comes through. “No is not an option” is how we work on Ryan Murphy television. Fortunately, my team, we’re all very good at our job so we haven’t heard “no” too much. But we do often have backup plans. In the shooting phase, we tell people to get “coverage,” meaning filming them singing different songs. We make sure the set is prepared with different options — we’ve had many situations where’s it’s been down to the wire and we’ve had to clear five alternate songs urgently to make sure that, by the time the episode is done, there is an option that is ready to be in the final mix. In this case, it would have been another version of “The Star-Spangled Banner.” But watching the scene, it was so critical in every way to have Whitney’s version. So thank God, we got it.

The Rugrats Movie (1998), rejecting David Bowie

Karyn Rachtman: The harder part of the job is when you get a great song and then the director decides he doesn’t want it after you did all this work. I had that happen with David Bowie, with The Rugrats Movie. The director [Igor Kovalyov] wanted Bowie, so I went and I made that happen. I flew to Bermuda and he gave us this song, “Sky Life,” that was unreleased. It’s so gorgeous and haunting.

You know how they say, “Never meet your heroes”? It’s not true. He was the most wonderful person I’ve ever met. When I was at his house, he had just painted a picture of Iggy Pop and he had a test print of it to approve, so it’s numbered 00. And he gave it to me. He wrote, “To Karyn, with all my love, David Bowie.” I cherish that with all my heart.

Now, mind you, the song was very sad, but it’s so beautiful. The director just said, “No.” Maybe they were scared to go back and say, “Can you make it a little bit more like this?” When you hear it, you’ll be like, “Oh, how could that have worked in Rugrats?” To an extent, we were all kind of like, “How are we going to make this work?” I feel like there was a way we could have.

And it was just me having to tell David Bowie’s camp that they didn’t want his song. He was very upset. They wanted me to come out in the press and say that it didn’t work out and that we loved David Bowie’s song, that kind of thing. It was bad. Because it was David Bowie, I was ultra sad. It just felt like, how could I be in this situation? He released it later [as “Safe”], a little bit different than what he was going to do for Rugrats. That was harder than any song I couldn’t get for a film. It was horrible.

The Marvelous Mrs. Maisel (2017-2019), obscure French and Hawaiian songs

Robin Urdan: Part of the music supervisor’s job is to be an investigator or researcher, really be a detective. With the internet, we can do so much more now than we ever did, using Twitter or finding people who know people who know people. When I started in this business in the ’90s, we had something called a Phonolog, the biggest book you’ve ever seen. It had every song with every songwriter and what recording it was on, and then we’d get pages sent to us to add in when things changed or new songs came in. We also went to Tower Records to look things up, and we would call ASCAP or BMI, but they would only give you the information on three songs per call. You’d have to hang up and call back — I had to hire an assistant to do it because you’d be on hold all day and couldn’t do any other work.

Mrs. Maisel is the most challenging and the most rewarding in that regard. Amy [Sherman-Palladino] and Dan [Palladino], they know music, they love music — they know what they want, and you do everything you can to not say, “No.” For season two, there was a scene in the French club, Madame Arthur’s, and I actually found one of the first trans [women] ever who performed in the club, Bambi. She emailed me this big long letter in French — thank God for Google Translate — and got information on what songs they played there, and Amy chose this song “C’est Paris” for a scene. French music is very different to clear — you have to go through every single writer or heir, or heir of an heir. Universal’s office in Paris couldn’t find one heir for two weeks, so I was calling them 24/7, and literally, at 1 o’clock in the morning before the shoot, I got the approval. There was no reason we didn’t think it would clear, but I lost so much sleep over it.

I’ve found hundreds of songs for Maisel. There was one where I called this man who’s now 97 years old, Ray Anthony, because it had his name down as the songwriter. He asked me to come over with the check and pay him, and I said, “Do you not have anybody that reps you?” He said, “No, I do this myself, but my brother will be coming over. I just got out of the shower. You can come over to my apartment,” and he told me where he lived and he gave me his address. It was pretty creepy. Somehow, some way, we found that he didn’t rep himself but we cleared it, we used it, everybody got paid.

Another one was a Hawaiian song, “Fish and Poi” by the Morgan Sisters. I couldn’t find the master, so I looked and looked and reached out to everybody and finally found the person who owned it, Eaton Magoon. He was in hospice. I was talking to his friend, who is the person I had reached out to, and he FaceTimed me from there: “Here you can see, he’s in hospice.” His lawyers sent me all the paperwork and they confirmed it. It was crazy and it was wonderful.

Better Call Saul (2015-2019), the music of Jimmy McGill

Thomas Golubic: Being able to figure out how music can best contribute to the storytelling is one of the hardest skills. Taste in music is lovely, but if you can’t tell how to utilize music to help tell a story, you’re not doing your job effectively.

A lot of it comes down to having a really thoughtful relationship with the script. It’s not dissimilar to what actors do — we spend a lot of time getting to know the characters. When we start, we want to figure out the general parameters, what worlds we want to be in, so we create mixtapes for each character. I use a program called Swinsian, which is like iTunes, and create a ton of mixes. We will, in our imaginations, match them up with where we think the character might go. A lot of those ideas end up being wrong, but the early mixes are important because they give us a lot of space to play with.

For instance, with Jimmy [McGill in Better Call Saul], we never really viewed him as being somebody who was really tied to a specific time period with music. The music we used for Jimmy in the early seasons was the music of how he viewed himself, things like Dave Brubeck’s “Unsquare Dance” that have a certain elegance to them and a certain mischievous quality to them. They’re positive and a little bit highbrow and they have a sense of playfulness. Whereas the truth is that Jimmy is much more funky.

So now he’s evolving from Jimmy McGill to Saul Goodman, and the music helps to punctuate those moments. We used Dennis Coffey’s “Scorpio” when he’s changing his suits and trying to get fired from Davis & Main. It shows the grittier side of him coming out, but we retained the fun because he’s enjoying himself. He picks up a lot from movies, and those tools become part of his spiel. A good example is the sequence where we used Vivaldi’s “Concerto for Strings in G” and it was a reference to the wonderful montage from All That Jazz. We did our own version of it using a lot of flutes, fifes and banjo — a ramshackle, second-generation Irish immigrant quality to it. It was a fun way of tethering the version of who he thinks he is, this superstar becoming the public defender that gets the job done, mixed with the reality of who he is.

We were really responding to the fact that Jimmy was projecting a version of himself that he didn’t fully believe and wanted to believe. And as the story evolved, it became clear that he wasn’t that, and the music began to reflect that naturally. A lot of the early ideas we had, some of them were really right on for where we ended up, but we didn’t know that at the time. It’s a very sensitive process.