It begins like clockwork each November.

Bing Crosby and his posse make themselves heard. It doesn’t matter who you are, where you live, or what you do: Bing attacks indiscriminately. (For me, it was the home goods section of a Target in North Carolina.)

It may be a “White Christmas” here, a “Silver Bells” there, but one way or another, an anointed bunch of 70-year old recordings will find their way into your ear. Crosby is the ghost of Christmas past, present, and future. Immortal, unchanging, crooning year after year the same as the year before.

Truthfully, congratulations are in order. You’ve done it, Bing. You won Christmas. You planted your sound in 1942 and your voice has echoed through supermarkets across America ever since. You’re what every musician strives to be: timeless. Quintessential.

Our addiction to this decades-old seasonal pageantry fascinates me. Why do we do it?

Are we homesick? Lazy? (What’s comfortable is easier than what’s new.) It could be nostalgia: a desire for a simpler time, colored by hazy memories of childhood warped by the childhoods we’ve seen portrayed in film. More cynically: it’s an almagamation of modern-day capitalism, copyright law, and romanticization of the American dream.

What’s the reason for the wheezin’?

Bah humbug! It’s time to let it go. There are too many talented musicians for us to keep on stabbing our ear holes.


In 2009, I took matters into my own hands. I cobbled together 20 tracks of the freshest, least-beaten-to-death holiday tunes I could find. I burned CDs for family and friends (Sharpie-ing on poorly-drawn snowmen) and designed album art which I printed on computer paper and scotch taped together. I creatively titled it Kyle’s Winter Mix.

People seemed to like it, word spread, so I made another one the next year. And the year after that. Until six years had passed and I’d compiled 120 tunes.

In 2011, after two years of distributing CDs, I moved to a new city. To keep the tradition alive, I developed a website to offer downloads. Year by year, that initial site has been destroyed, rebuilt, and reshaped up to its current form.

An illustration of a CD case
  • CDs and doodles
An illustration of a laptop with a two-column grid
An illustration of a laptop with a three-column grid
  • Redesigned mini-site
  • Moved to subdomain of
  • Added download links to past mixes
  • Added comments via Disqus
An illustration of a laptop, tablet, and phone with a slider layout
  • Completely rebuilt responsive site
  • Touch-friendly slider layout
  • Displayed complete tracklists for each year
  • Implemented basic audio streaming
  • Redesigned past album art for consistency
An illustration of a laptop, tablet, and phone with a scrolling layout
  • Hosted on new domain—
  • Updated layout featuring fixed sidebar
  • Switched from slider to scroll for easier navigation
  • Optimized audio files for streaming and download
  • Refactored code for easier future edits
This is the real site! Play with it!
Or open in a new tab. is a single page site. It’s responsive; the track titles and artists are dynamically pulled from the .mp3 files; songs can be streamed directly on the webpage, downloaded as zipped album, or individually by right-clicking the track name; and the setup is easily extendable—adding a new year is as simple as uploading a folder of mp3s and a background image.

Mastering transitions

In 2011, I had assembled all the tracks I liked, but listening to the album as a whole, the flow just wasn’t there. I shuffled and reshuffled, groping through the dark and hoping to latch onto a solution, when suddenly I was struck: what if I used music theory to guide which track comes next?

I analyzed the starting and ending keys of each song, using common modulations to gracefully transition from one track to the next. It worked beautifully.

What makes a “good” transition?

Music has no rules, but it does have conventions. Click or tap the letter names on the circle of fifths to see common key changes between major keys.

Go to the subdominant (up a fourth). Very common. Bridges and middle sections of songs are often in the subdominant.

Go to the dominant (up a fifth). Also common. Often used to build tension before resolving back to the home key.

Go up a half-step. Ups the ante. Hokey if overused.

Go down a half-step. Feels like sinking into a big, plush armchair. Can relax tension or elevate mysteriousness.

Go up or down a whole-step. Similar to modulating by half-step, but more stable and triumphant.

The music has evolved along with the design, each year becoming a little more diverse than the last: the most recent mix includes a Spanish celebration of el año viejo, a Renaissance-era French carol, Swedish electrofolk, some j-pop wishing you a very merry Kurisumasu, and an 80s-era commissioned-for-Black-History-Month-by-Miller-High-Life-and-now-only-exists-on-YouTube gospel rock anthem sung by Al Green and Deniece Williams backed by Patti Austin, Roberta Flack, and Melba Moore. (Seriously, watch this video. It’ll make you smile.)

Album art

Each album cover features a vintage postcard of somewhere I visited that year. It’s a fun easter egg for my close friends, and a yearly reminder of how fortunate I’ve been to travel.

A vintage postcard of Chicago.


A vintage postcard of the Biltmore Estate near Asheville, NC.


A vintage postcard of the Blue Ridge mountains.

Blue Ridge

A vintage postcard of Key West, FL.

Key West

A vintage postcard of cherry blossoms in front of the Washington monument.

Washington, DC

A vintage postcard of the Eiffel Tower in Paris, France.



This project has always been simply a way to spread music I enjoy to the people I love, and in that regard I couldn’t be more pleased with its success: I’ve had friends who I haven’t seen since high school message me and say how much they love listening to my mix each December. Family members halfway across the globe telling me which songs brought them joy.

Seeking out new music each year has led me to discover talented artists I wouldn’t have known about otherwise. I’ve even come across recordings from Bing Crosby’s era that are rarely played today—ones that don’t carry the weight of familiarity.

Ten years later, dear old Bing’s omnipresence seems diminished, if only slightly. Despite fierce, repeated protests, my mom put on his album this past winter when I was home. Maybe it’s because I’m an adult now, living on my own in a city hundreds of miles from home, but for a moment, listening to “White Christmas” in my parents’ living room, I understood why his music has stayed with us for so long.

I do actual work, too. Check out the Dropbox and Swiftype case studies, which do not include holiday puns. Read about me or go play Jingle Bells.