1.”Gymnopedie No. 1″ by Erik Satie

It’s important to start your bedtime playlist with a song by an old dead white guy. I first heard this particular Erik Satie song in that Angelina Jolie movie, Gia. Now I’m not sure if it’s because I was on enough muscle relaxers to tranquilize a baby elephant or if this song was really that chill but I recall sleeping like a baby that night. Unfortunately, I forgot all about the song and its amazing sleeping powers until I heard it in a hipster clothing store years later. Having no shame (and, more importantly, no access to Shazam) I went up to the employee and asked him who “sang” this track. He was just like, “What? Don’t talk to me. Just look at the iPod,” and when I found out who it was, I downloaded it right when I got home. It’s earned a permanent spot on every nighttime playlist since.

2. “Blue In Green” by Miles Davis

You know how when some people describe their favorite music, they say weird things like, “It feeds my soul!” and you’re just like, “Excuse me?” Well, Some Kind Of Blue by Miles Davis is a record that feeds my soul. I don’t know how else to explain it. It just transports me to another (happier and mellow) place. I always listen to it after I’ve had a bad day, preferably in the bath or when I’m in bed, and it makes me feel so warm and safe. Even now, listening to it on my headphones at this coffee shop where I’m writing this post, I’m getting chills and it’s super embarrassing.

3. “Like An Ion” by Sciflyer

I first heard this song in 2004 on one of those music samplers you would get for free in a magazine. Most of the bands would suck but occasionally you would find a track by some obscure band that you would obsess over. I was just beginning to really get into shoegaze, a genre of music made most known by bands like My Bloody Valentine and Slowdive, and I was instantly struck by the distant vocals and dreamy guitars in this song. I remember driving back from my college orientation in Orange County with my mom listening to this slice of hazy heaven and being lulled to sleep by it. Have you ever tried to sleep during a car ride with your mom? It’s like really freaking hard.

4.”Blue Motel Room” by Joni Mitchell

I’m convinced that Joni Mitchell was sent to this earth to make me feel things. Her music is better than any therapy session I could conjure, especially the songs on Blue and Hejira. She really wasn’t screwing around, was she? She wanted her listeners to experience all the joy and heartbreak with her. We couldn’t get away with anything. She held up a mirror to our life so perfectly and wouldn’t shy away from exposing painful universal truths.

5.”Asleep” by The Smiths

This is the anthem of sentimental gay boys everywhere. I mean, how could I not include it on the list? If Joni Mitchell is your emotional mom who believes in the healing powers of crystals, Morrissey is totally your closeted father who cries himself to sleep every night.

6.”Little Star” by Stina Nordenstam

I found this song on the life-altering Romeo + Juliet soundtrack and immediately put it in my nighttime rotation. It starts off all delicate, like someone is tickling you with a feather, but then it becomes all jazzy and spiritual?! It’s total Mom Music, which is a genre of music I can wholeheartedly get behind. (Except for Goyte.)

7.”Four Corners” by The Sea And Cake

The Sea And Cake is a shockingly dull band. All the band members must’ve gotten together and been like, “We want to make music that renders people unconscious. How do we do that?” No shade though because what their music lacks in energy, it makes up for in being the perfect band to fall asleep to. Just don’t listen to them any other time, okay? Seriously.

8. “Willie Deadwilder” by Cat Power

When putting together a playlist for bedtime, it’s important to end it with a lengthy song just in case you can’t fall asleep right away. I swear, it’s the worst feeling when the playlist ends and you’re still GODDAMN AWAKE. “Willie Deadwilder” by Cat Power is almost 20 minutes long so if you’re not asleep by the time it ends, you have my permission to screw the playlist and take an Ambien instead. I tried, y’all!

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Chilly Gonzales takes the stage at the Pigalle Club, a Forties-style dinner and cabaret spot in London’s West End (circular tables, low ceilings, regular intervals of green velvet), and assumes his place at the piano. He is wearing a brown knee-length silk robe with matching trousers and a pair of generously cushioned slippers. His hands are encased in pristine white gloves. With shadowy deep-set eyes and slicked back hair, he is the very image of the brooding piano maestro.

He eases into a medley of slow, spare classical pieces. The music starts off somber and restrained, but his fingers move with such fluidity that they can’t resist adding little flourishes here and there. The embellishments begin to mount up. What opened with an air of great solemnity is now becoming increasingly comical. Now he’s playing a blues standard with one hand, a blur of white hammering away at the lower octaves.

He wraps it up and turns to confront his audience. “Hi, I’m Chilly Gonzales. If you don’t know me, I’m a Grammy-nominated producer.” This is true. He continues: “I hold the Guinness world record for longest continuous piano concert at 27 hours.” This is also true. “I’ve got a lot of famous friends.” He pauses for effect, then performs a modest raise of the shoulders. “In France, where I live, they call me un génie musicale.”

In 2004, Gonzales, who is neither French nor Hispanic but Canadian and whose real name is Jason Beck, released Solo Piano, an album of concise minimalist classical numbers in the vein of Erik Satie which gave substance to the génie musicale claim. Those who came to know Gonzales through that album – his best-selling by some margin – would have been shocked to learn that the author of those beautiful, delicate pieces had previously made, among other things, a gleefully profane lo-fi rap record called The Entertainist.

It’s not entirely surprising that a musician who rolls out his “unfuckwithable resume” at the beginning of a show, and makes unabashed reference to his musical genius at every opportunity, should dabble with rap. Rapping is, after all, the art of the inflated brag. The Sugarhill Gang were extolling their globally-endorsed sexual prowess and enviable motoring options as hip-hop drew its first breath, and given the amount of hot air that’s been blown over 4/4 beats since then, it’s no wonder the ice caps are melting.

Gonzales embraces the spirit of boastfulness on The Entertainist and its more lavishly produced follow-up, Presidential Suite, although in Gonzoworld the line between brag and self-skewering gag is always porous. Yes, he may be “the greatest entertainer of the year”, but he is also “the worst MC” who gets “more pussy than a priest”. He is “the prankster Frank Sinatra”, a “combination of Joe Stalin and Woody Allen”, whom you may address as “Fuckeye” or “the one-eyed Jew”. Or “Chilly Chaplin”. Or “Santa Klaus Kinski”, because he spent a few years living in Berlin.

“I am the worst MC” is at once a villainous sneer and an admission that Gonzales’ rapping abilities circa 2000 left something to be desired. In fact, as he demonstrates during tonight’s show, Gonzales is a pretty good rapper – stylistically derivative perhaps, but deft, playful and always entertaining. He spouts vast jets of nonsense in his rhymes but somehow manages to be more upfront than any other rapper you’d care to name.

Musicians rarely speak about, let alone lyricize, the shallow calculations that often underscore big career decisions, yet here is Gonzales on why he left Canada for Berlin: “I still remember when it first occurred to me./ Fuck it, I’m gonna move to Germany./ I don’t speak German, screw it/ But hey! I’m Jewish/ And I need a new press angle and that should do it.”

These kinds of outrageous proclamations make listening to Gonzales, or attending one of his shows, enormously fun. His almost pathological frankness presents an interesting challenge, however, when it comes to interviewing the guy. Any criticism you’d level at him has already been anticipated, and slyly underlined, in his music, or on other platforms. When he released Soft Power, his paean to Seventies soft-rock, in 2008, he posted a video online in which a Mercury label honcho begs him to take singing lessons to soften his harsh Montrealer tones. In the clip he circulated to promote his London dates, Gonzales tells a buffoonish interviewer, also played by Jason Beck, that although he “owns” France, he remains an underdog in England, adding: “I’m not a young man anymore. This could be my last chance.”

So why all the second-guessing?