I was driving with my brother, playing him my summer road-trip playlist and explaining the rules that I follow when creating it:

Me: “This first song is by Prince; I like to incorporate songs by artists who passed away in the previous year.”

My brother, scrolling through my list: “Green Day? Did one of the guys in Green Day die?!?”

Me: “No. I also include songs by artists who someone in the family has seen in the past year.”

My brother: “CeeLo Green? When did you see him?”

Me: “I didn’t; I just like that song.”

My brother: “Why is there so much ‘Hamilton’ music?”

Me: “JUST LISTEN TO THE PLAYLIST!!!”

So I should probably explain for you, faithful blog follower, and definitely for my brother. For the last few years, I have made a playlist for each of our family vacations, following an increasingly elaborate set of rules that I totally made up and that I thought would mean something to my family but apparently matters only to me. Not that I am bitter. Here’s how I choose songs:

1. First, I start with an overall theme. For example, in 2016, my son was graduating high school, so the obvious choice was songs from the Disney Channel “High School Musical” movies. This year’s theme was “Hamilton” because (a) three of us saw the show in Chicago, and (b) our youngest child obsessively listened to it at home and knows all the lyrics.

2. I also include artists who have passed away recently. This year’s list included Prince, Glenn Frey, Chuck Berry, David Bowie, and George Michael.

3. Musicians who we have seen in concert in the last year make the cut.

4. Songs that have a connection to the places were are traveling to are in the mix.

5. Songs that have a connection to our family,  for example, from a TV show or movie we’ve viewed.

6. Songs that have no obvious meaning but that I like are included. (Hey, I’m the DJ.)

Those are the main rules. Broadly speaking, there will be mostly fun driving songs with a few slower ones at the end, there will be songs that not everyone in the family enjoys but that someone will love, and there will be Taylor Swift (personal preference; my wife knows about my Taylor Swift obsession, so it’s not creepy). Sometimes, songs just don’t work with the rest of the list. In 2016, I included a new song called “Her Mercy” by Glen Hansard, one of my lovely wife Jen’s faves, and for whatever reason, it didn’t fit. The song before it was from “High School Musical,” the song after it was loud and fast, and it just kind of sat there in the middle. I really like it and would recommend Glen Hansard to anyone, but that was a screwup on my part.

This year, we went to Colorado. Our son stayed behind to work a job and earn some money for college, so it was Jen, the girls, and me. We started in Denver and moved up through Boulder to Estes Park and Rocky Mountain National Park.

Here’s the list. (I still slip and call it a “mixtape” and get ridiculed mercilessly for being old. I remember a time when creating a mixtape involved having a double-cassette-deck stereo; I’d elaborate on the process, but I’m sure nobody under age 40 cares.)

Colorado 2017 Playlist!

1. “Let’s Go Crazy,” Prince & The Revolution, Purple Rain. So sad to see such a talented artist die relatively young, especially because he did us short people so proud. This song has a great start (“Dearly beloved, we are gathered here today to get through this thing called life”), but frankly, it kind of drags on the playlist when it settles into the rest of the song.

2. “The Story of Tonight,” Lin-Manuel Miranda, Daveed Diggs, Okieriete Onaodowan, and Anthony Ramos, Hamilton. “Raise a glass to freedom, they’ll tell the story of tonight…” Still setting the mood for the road trip. A great little song about the beginnings of the American Revolution.

3. “Welcome to New York,” Taylor Swift, 1989. Our middle child spent a week in NYC with the high school drama club; this was for her. Also, I’m a big fan of Taylor Swift; this is no secret.

4. “Castle on the Hill,” Ed Sheeran, Divide. Just because I like this song. I placed it after the Taylor Swift song because they have toured and recorded a song together (“Everything Has Changed”).

5. “Should I Stay or Should I Go,” The Clash, Combat Rock. This was the theme song to Season 1 of Stranger Things, a Netflix show that my kids forced me to watch. Not to get too deep here, but I put it after the Ed Sheeran song about longing for our childhood because the TV show takes place in 1983, when I was 12 years old, the same age as the main characters in the show. Plus, I got to see one of the Clash’s founding members in concert (Mick Jones when he was in Big Audio Dynamite).

6. “Move Along,” The All-American Rejects, Move Along. Great pop punk song that everyone can scream along with on a car ride. Our youngest daughter and I saw them open for Blink-182 within the past year.

7. “Still Breathing,” Green Day, Revolution Radio. I took both of our daughters to see Green Day earlier this year (my ears are still recovering). This new song off their latest album keeps me going, when I’m running and in life generally. Another pop-punk car-ride screamer.

8. “Say You Won’t Let Go,” James Arthur, Back From the Edge. Zero connections to this song; I just like it. A love song to my wife. Turned out, though, that our youngest hated this song because all the kids in her class at school would request that the teacher play it when he allowed them to listen to music. Well, too bad, Dad’s in charge.

9. “Rocky Mountain High,” John Denver, Rocky Mountain High. Too obvious? This is required listening for a trip to the Rockies. Interesting side note: John Denver’s real last name was Deutschendorf; an LA club owner recommended that he change it to Denver. He didn’t actually visit Colorado until 7 years after he picked up the stage name. (“He was born in the summer of his 27th year…”)

10. “Rocky Mountain Way,” Joe Walsh, The Smoker You Drink, the Player You Get. Also too obvious. Pretty sure Joe Walsh is not talking about the mountains here (“couldn’t get much higher…”). We did see a few marijuana dispensaries while in Colorado. Jen and I got to see Joe Walsh in concert when he was touring with the Eagles about 10 years ago.

11. “You’ll Be Back,” Jonathan Groff, Hamilton. One of the King George songs on the soundtrack, definitely the comic relief of the show. (“You’ll be back, time will tell, you’ll remember that I served you well; Oceans rise, empires fall, we have seen each other through it all; And when push comes to shove, I will send a fully armed battalion to remind you of my love!”) Jonathan Groff is a family favorite; he was the voice of Kristoff in Frozen and Jessie St. James in Glee. 

12. “On Hold,” The xx, I See You. Another song with no connections. I like the way it sounds, and when a song samples Hall and Oates’ cheesy ’80s tune “I Can’t Go for That (No Can Do),” I’m in.

13. “The Weekend,” Modern Baseball, Sports. This song and this band remind me of my high school and college days. Hard to believe, kids, but there was a time when I went out to parties and had girl problems.

14. “In a Drawer,” Band of Horses, Why Are You OK. Before our middle child got her drivers license, I would drive her and her friends home from school. When this song came on the radio, she would complain about it (“It’s about a guy finding something in a drawer!”), but I knew that secretly she loved it and that it was destined to end up on our playlist. That’s the kind of keenly attuned dad I am.

15. “Good Help (Is So Hard to Find),” Death Cab for Cutie, Kintsugi. Great song with a good beat. Also, it sounds to me like a political statement (“You’ll never have to hear the word ‘no’ if you keep all your friends on the payroll”).

16. “Wish You Were Here,” Pink Floyd, Wish You Were Here. Taken at face value, this one was for our son, who couldn’t make the trip, the first time one of our kids missed a vacation. Personally, this song hits me because it reminds me of a childhood friend who introduced me to Pink Floyd who died while we were in college. Surprisingly, this song doesn’t work on the playlist; there’s too long of a buildup, and it’s too slow.

17. “All We Ever Knew,” The Head and the Heart, Signs of Light. Another popular song on the drive home from school (thanks, WXRT!). I hear about three or four distinct songs within this one every time I listen to it: there’s a slow part at the start of each verse, a pickup at the chorus, and a nonsensical singalong portion (“La la la la la la…”), plus a bridge that sounds like another song.

18. “Best of Wives and Best of Women,” Lin-Manuel Miranda and Phillipa Soo, Hamilton. I didn’t include any of the Hamilton songs that actually make me cry, but this one comes close. Alexander is about to go off to a duel with Aaron Burr, and his wife Eliza asks him to come back to bed. He tells her he’ll be back soon, and as she turns away, he calls out, “Hey, best of wives and best of women.” That’s an actual quote from the letter Hamilton wrote to Eliza on the event of his death.

19. “Mom,” Meghan Trainor, Thank You. Jen had been thinking and worrying about her own mother as we left for the trip. It’s also a fun song for moms and daughters to sing together (and I got to hear mom and daughters singing together loudly on this trip).

20. “F@#k You,” CeeLo Green, The Lady Killer. Well, ahem. Yes. We allow swearing in our family if you are singing along with a song. This is a great tune for a windows-down drive, except you might want to keep the windows up when the chorus comes around.

21. “Already Gone,” The Eagles, On the Border. Glenn Frey’s passing caught me off guard. I had seen him solo in a very strange setting: my brother-in-law’s company picnic up in the Santa Monica mountains sometime in the early 2000s. I saw Don Henley solo in the early 1990s, and I got to see the reunited Eagles about a decade ago. Frey was a great showman and a solid musician, and it can be argued that the Eagles are America’s greatest rock band. But that’s a story for another blog post.

22. “Johnny B. Goode,” Chuck Berry, Chuck Berry Is On Top. I was lucky enough to see Chuck Berry in concert before he passed, back when I lived in St. Louis. He was in his 70s and would play about once a month in the basement of Blueberry Hill, a restaurant in University City, MO. I had been told that he was very hit-or-miss; some shows were great, but in others he was disinterested, ornery, and ready to bolt early. I got a great show. What was fascinating was that he would start with a guitar riff (and if you know Chuck Berry songs, you know there are basically two riffs that his songs start with), and the other guitarist would figure out what song he was playing and yell it out to the pianist and drummer. Fun stuff.

23. “Modern Love,” David Bowie, Let’s Dance. Seriously, it’s getting harder to take, this aging and having all my music crushes die. David Bowie? Come on. Was there anyone more willing to reinvent himself and be different at the risk of ridicule?

24. “Don’t Let the Sun Go Down on Me,” George Michael featuring Elton John, Duets. Okay,  I get it, everyone dies. But George Michael? I don’t have to remind my faithful readers that Wham! was my first concert experience. I could have chosen any Wham!/solo song, but I went with this one because it’s a fun singalong and the video was recorded live in Chicago, my home base.

25. “Miles Away,” Goldfinger, Goldfinger. For years, I had this album on a poorly-recorded cassette, and I had practically forgotten about it. Then our youngest child, who fell head over heels for Blink-182, Green Day, and Fall Out Boy, started agitating for more pop punk music. I finally broke this album out for her and rediscovered how good it was. Plus, we were literally going, ahem, miles away from our home on this trip.

26. “Cynical,” Blink-182, California. I took our youngest to see Blink-182 in concert, and my ears recovered just in time for us to see Green Day. The reconstituted Blink-182 is unfortunately missing Tom DeLonge, their great co-lead singer, but Mark Hoppus makes this song off their most recent album sound as good as any of their early stuff.

27. “Packed Powder,” Blind Pilot, And Then Like Lions. How many indie bands can Portland, OR, produce? Here’s another. Love the feel of this song. “I started working as a tour guide, I thought it would make me believe my own words…” I am purposely winding the album down with softer songs at this point.

28. “Set ‘Em Free, Pt. 1,” Akron/Family, Set ‘Em Wild, Set ‘Em Free. This one was a holdover from the previous year’s playlist, when our oldest went to college. I heard it (of all places) in a tire commercial. I interpret it to be about letting our kids grow and go. “Set them free, set them up, and let them be their own release, And when it’s time you can begin to let them breathe…”

29. “Who Lives, Who Dies, Who Tells Your Story,” the cast of “Hamilton,” Hamilton. I lied: I did include a song from the musical that brings me to tears. It tells the story of Eliza and Alexander, but it’s also a message about our limited time in this world from Lin-Manuel Miranda to all of us: “And when you’re gone, who remembers your name? Who keeps your flame?”; “And when my time is up, have I done enough?”

30. “Nightswimming,” R.E.M., Automatic for the People. I always planned on ending a playlist with this quiet song. There was a time before iTunes and Spotify when record companies would release albums, often on Tuesdays, and fans of a band would line up (yes, line up!) outside of record stores on release dates to buy the latest albums. When I was in college, R.E.M. was one of those bands for me; the band has retired, which is a bizarre thing to do for a band that produced so much vibrant music over the decades. The song “Everybody Hurts” got more airplay off of this album, but this song meant more to me. I think of Jen and me when I hear it, about how lucky we are to have known each other since we were teenagers. “Nightswimming, remembering that night, September’s coming soon, I’m pining for the moon; And what if there were two side by side in orbit around the fairest sun?”