Every day is a good reason to put on a specific song. 

The following list is a mixture of songs about a specific event, date or season. Or somehow tied to that day. 

There are certain artists that could be included every month. Tom Waits, Prince, The Beatles, OutKast, Johnny Cash, Green Day, Local H, Wilco, The Decembrists, Bruce Springsteen, Cake, Ramones and others have multiple songs tied to specific events, months, and seasons. The list attempts to have as many artists as possible for better variety. 

There are multiple songs related to the Bears, Blackhawks, Bulls, Cubs and White Sox because those are the teams I like. 

There are some concert recordings important enough to include. Those are placed on the date of recording. 

There are some influential records important enough to include. Those are places on the date of recording or release. 

Here’s the playlist on Spotify. It’s at the end too. Not every song on the list is included due to rights issues. Some videos are sprinkled throughout. 

Enjoy. Listen to new music. Listen to old music. Listen to different stuff every single day. 

January 

1 – U2 “New Year’s Day”

Come on, just admit this is a great song that you think of at least once on New Year’s Day. It also has all of the hallmarks of U2’s best songs. 

2 – Bill Monroe & His Blue Grass Boys “Footprints In The Snow”

I’m a sucker for upbeat, tragic songs that sound like they’ve been around forever. Or before copyright exists as we know it. 

3 – Nick Cave and the Bad Seeds “Fifteen Feet of Pure White Snow”

It’s not really about snow but it’s about snow.

4 – Taco Cat “Snow Day”

This mid 2010s garage pop rocker does in fact sound like a fun snow day. 

5 – The Halo Benders “Snowfall”

Of course the side project of two dudes from the Northwest, Built to Spill’s Doug Martsch and Beat Happening’s Calvin Johnson, have a good snow based song. 

6 – Bad Religion “American Jesus” 

Living in Washington, D.C. on January 6 sucks. 

7 – Muddy Waters “Hoochie Coochie Man”

Without Muddy and Chess Records, most of the artists that picked up a guitar since January 7, 1954, the recording date of Waters’ signature song, would sound very different. 

8 – Pearl Jam “Jeremy”

A hit song about a real-life school shooting in 1991, released on Pearl Jam’s debut later that year, remains depressingly relevant. 

9 – Loving “January” 

Our first instrumental of the list. There are quite a few. At one point, this entire project was mostly instrumentals. There are more than enough songs named after specific dates, months, season and weather patterns to make a list of 365. But most, at least most discovered through this project, are not good. Loving’s “January” is fantastic. If it was titled “July” it probably wouldn’t be included. 

10 – David Bowie “Blackstar”

The best sign-off of all-time?

11 – Nirvana “Smells Like Teen Spirit”

The best SNL musical performance of the 90s?

12 – Sam Cooke “Having a Party”

From Live at the Harlem Square Club, 1963. Who wouldn’t want to party with Sam Cooke in Miami in January? 

13 – Johnny Cash “Folsom Prison Blues”

From At Folsom Prison. The best live albums are shows you wish you were at or shows you were very glad to miss. 

14 – Warren Zevon “Boom Boom Mancini” 

More songs need to be about boxing matches. This one revolves around watching the Ray Mancini Bobby Chacon January 14, 1984 fight. 

15 – Public Enemy “By The Time I Get To Arizona” 

The best song about Martin Luther King Jr. Day. Sometimes you need to have a violent message to honor someone who believed in non-violence. 

16 – Slow Fiction “January” 

One of the newest songs on the list, Slow Fiction’s 2024 ode to the first month of the year is a fine reason to keep this up-and-coming act on your radar. 

17 – R.E.M. “Man On the Moon”

You know you’ve made it when R.E.M. centers a song around you. There’s a solid argument that the 1999 movie of the same name doesn’t happen without this 1992 hit. How was this a hit?

18 – Beirut “January 18th”

There are certain artists that embody seasons. Beirut is one of those artists. The seasonal effects are more pronounced in headphones and on bar jukeboxes than home stereors. 

19 – Offset, Metro Boomin “Ric Flair Drip” 

The Dirtiest Player in the Game is honored on the date of the Royal Rumble 92. Unlike most others, we are fair to Flair.

20 – Radiohead “2+2=5”

Hail to the thief. 

21 – The 5th Dimension “Aquarius/Let the Sunshine In”

Happy Aquarius season! 

22 – Filter “Hey Man, Nice Shot” 

Bud Dwyer. 

23 – Dean Martin “June In January”

The coolest member of the Rat Pack wants you to feel warm in the cold. 

24 – Babe City “January” 

Another new act, another great slow dirge of a rock song centered around January. This one sounds like pretty sludge. 

25 – Flatfoot 56 “Winter in Chicago”

I have also been stuck on Lake Shore Drive in the winter in Chicago! I have also watched the Hawks on the television in the winter in Chicago! 

26 – The 1985 Chicago Bears “Super Bowl Shuffle”

The greatest sports anthem on the day of the most one-sided Super Bowl victory. 

27 – Sweet “Ballroom Blitz”

Inspired by a real-life incident of a ballroom blitz. Included for Wayne’s World reasons. When I was younger I thought it was insane a band would think they could get a record deal by performing covers. I was incredibly wrong. 

28 – Prince “Purple Rain”

The best song from the best Super Bowl halftime show. 

29 – Mojo Nixon “Not As Much As Football”

This is the song liberal football fans need to make their own. 

30 – Whyte Horses “The Snowfalls”

This song is one of the reasons projects like this exists. I ‘discovered’ this song in the research and now I’m regularly listening to this modern psychedelic band.

31 – Creedence Clearwater Revival “Fortune Son” 

A simple, relevant reminder of the deadliest day of the Vietnam War.

February 

1 – Grateful Dead “Cosmic Charlie” 

Most people give up their New Year’s Resolutions by February 1. I do not. This is a reminder that I’m still trying. I’ve been trying to ‘get’ the Dead for 20+ years. So I’ll listen to a song of theirs that mentions February 1 on February 1. 

2 – Bruce Springsteen “Glory Days”

It’s not good to live in the past. But since the National League was formed on February 2, 1876 and baseball is the sport that most lives in the past, this Bruce banger tangentially about America’s pastime/getting wasted on beer in your local bar, on the album that features a giant American flag and a demic clad butt on the cover, is appropriate. 

3 – Jimmie Rodgers “Blue Yodel No. 1” 

This foundational American song was released on February 3, 1928. It’s still great. In addition to the iconic yodeling, there’s proud pronouncement of virility and willingness to murder. It’s influenced most of the best country and folk music of the last 100 years. 

4 – OutKast “Rosa Parks”

The story of Rosa Parks’ (or her lawyers) reaction to one of OutKast’s signature song is worth a deep dive. 

5 – Architecture In Helsinki “One Heavy February” 

Slightly less than one minute of instrumental cheery pop. 

6 – Gil Scott-Heron “Winter in America”

Watch 1983’s Black Wax, a documentary/walking tour of DC with Scott-Heron and you’ll have a renewed appreciation for the poet, musician and activist. It’s available for free on YouTube. 

7 – TV on the Radio “Winter” 

This non-single from TVOTR’s most recent album, 2014’s Seeds (yes, it’s been more than a decade), sounds like a demo in the best sense.  

8 – Nico “Winter Song”

Some seasonally appropriate drama. 

9 – Kendrick Lamar “Not Like Us”

The best song from the second-best Super Bowl halftime show. 

10 – Amy Winehouse “Rehab”

The best Grammy performance. 

11 – Tori Amos “Winter”  

A gorgeous and haunting song perfectly suited for Mick Foley. 

12 – Percussions “February 2014” 

The ideal type of electronic music for working, working out, hacking, etc. 

13 – Foo Fighters “February Stars” 

It’s not fair for anyone to wish for a different version of a band but can you even imaging how good Foo Fighters would be if they sounded anything remotely like their first two records? Related, is this about Kurt? It’s probably about Kurt. 

14 – My Bloody Valentine “Loveless”

For the lovelorn on the most romantic day of the year.

15 – Billy Bragg “Valentine’s Day Is Over”

For the lovelorn on the least romantic day of the year. 

16 – Local H “Another February” 

I have also dug out my car from the snow. 

17 – Beach Bunny “February”

18 – Ray Charles “What I’d Say”

19 – Fleet Foxes “White Winter Hymnal”

20 – Ass Ponys “Last Night It Snowed”

21 – The Beta Band “Dry The Rain” 

The rainiest day in Chicago in 1997, the year this song was released, was May 21. This became a Chicago song due to its use in 2000’s High Fidelity. 

22 – Jimmy Buffett “Margaritaville” 

Parotheads rejoice, it’s National Margarita Day!

23 – Johnny Cash “The Ballad of Ira Hayes” 

24 – Julee Cruise “Falling”

Dale Cooper is forever pulling into Twin Peaks.

25 – Baula “February 2018”

26 – Neil Young “Winterlong”

27 – Japanese Breakfast “Winter in LA”

28 – Mineral “February” 

March

1 – The Dodos “Winter”

2 – George Strait “All My Exes Live in Texas”

In honor of Texas Independence Day. 

3 – Lady Gaga and Beyonce “Telephone” 

Happy birthday, Alexander Graham Bell!

4 – Morphine “Radar”

The older I get the more I appreciate Morphine and that can’t be a good sign. 

5 – Big Black “Kasimir S. Pulaski Day”

Happy Kasimir S. Pulaski Day! 

6 – Sufjan Stevens “Casimir Pulaski Day”

Happy Casimir Pulaski Day! 

7 – Julie London “Melancholy March” 

8 – The Carter Family “March Winds Goin’ to Blow My Blues All Away”

9 – Skullcrusher “March” 

10 – Antonio Carlos Jobim “Waters of March”

11 – 311 “Down”

Chill.

12 – Bo Burnham “All Eyes On Me” 

The only art that’s legitimately great because of Covid.

13 – Sons of Kemet “My Queen is Harriet Tubman” 

Happy birthday, Harriet Tubman! (Not tied to this date specifically, just the month of March)

14 – Neutral Milk Hotel “Holland, 1945”

A good reminder that all Nazis are evil. 

15 – Saul Williams “Act III Scene 2 (Shakespeare)”

Happy birthday, William Shakespeare! Also a good reminder to stand up to evil. 

16 – Jim Johnston “Stone Cold Steve Austin”

Gimme a hell yeah!

17 – Thin Lizzy “Whiskey in the Jar” 

Happy St. Patrick’s Day!

18 – Treasures “March 18th”

19 – System of a Down “B.Y.O.B.”

On the date of the start of the Iraq War, a reminder of who typically fights these wars. 

20 – The Cranberries “Zombie” 

In honor of the March 20, 1993 victims in The Troubles. 

21 – Tom Waits “Town with No Cheer”

22 – The Dixie Cups “Chapel of Love”

23 – Elliott Smith “Miss Misery”

The most uncomfortable and beautiful Academy Awards performance.

24 – Max Richter “Spring 1 – 2012”

25 – Angel Olsen “Spring”

26 – Mott the Hoople “Ballad of Mott the Hoople”

27 – Future “March Madness” 

The NCAA tournament deserves at least a mention. 

28 – The Clash “London Calling”

29 – Frightened Rabbit “Late March, Death March”

30 – Ruth Etting “March Winds and April Showers”

31 – Selena “Dreaming of You”

April 

1 – Rufus Wainwright “April Fools”

2 – Eddie Lang “April Kisses” 

3 – Daniel Knox “April 3rd”

4 – The Jesus and Mary Chain “April Skies” 

5 – Neil Young “My My, Hey Hey (Out of the Blue)”

I did my best not to center this thing around death and/or Nirvana but not putting this here would be inappropriate. 

6 – ABBA “Waterloo”

The most important Eurovision performance. 

7 – Gia Margaret “April to April”

8 – Hefner “The Day That Thatcher Dies”

We need more songs celebrating the future death of people that made life more difficult. 

9 – Thad Jones “April in Paris”

10 – Aretha Franklin “Respect”

11 – Charlie XCX “Spring breakers”

12 – Donna Summer “Spring Affair”

13 – Clifford Brown, Max Roach “Joy Spring”

14 – Richard James, Katia Labeque, Marielle Labeque “Avril 14”

Aphex Twin’s image and art does not at all match it’s beautiful music. 

15 – Roy Acuff “The Great Titanic”

Ships sink. Hearts do not go on. 

16 – Bob Wills “New San Antonio Rose”

17 – Gia Margaret “April to April” 

18 – Beastie Boys “Paul Revere” 

Happy Paul Revere’s midnight ride to you and yours! 

19 – Chuck Berry “Roll Over Beethoven”

Something about a new sound…

20 – Dr. Dre and Snoop Dogg “Nuthin’ But A “G” Thang”

This was one of the toughest days to pick. There’s no shortage of 4/20 related songs so here’s a song tangentially related to 4/20 on one of the biggest selling records and the best record titled The Chronic. 

21 – Eminem “Cum On Everybody” 

Not enough songs reference the Loch Ness Monster.

22 – The Flaming Lips “Do You Realize??” 

Happy Oklahoma Day!

23 – Ramones “Blitzkrieg Bop” 

For a few years, Ramones records dominated our family stereo. The first song on their debut remains perfect. 

24 – Les Baxter “April In Portugal”  

25 – of Montreal “The Problem with April”

26 – The Smiths “Panic” 

Most Smiths’ songs are too dramatic but when you’re singing about Chernobyl it’s warranted. 

27 – Lydian Dominant “April in Rome”

28 – Cheap Trick “I Want You to Want Me”

The best new rock and roll song from a live album?

29 – Daft Punk “Robot Rock”

Right now ‘robot music’ is dominating our family stereo. This live track from Daft Punk’s historic mid 2000s tour kicks off the record. It’s on April 29 since it the French duo introduced their pyramid at Coachella 2006. 

30 – Nick Drake “Pink Moon” 

The date of the April 1999 full moon, aka the pink moon, the year Nick Drake became a relative household name thanks to a Volkswagen commercial. 

31 – Judy Garland “April Showers”

May

1 – Shellac “Prayer to God” 

Get on your knees, it’s the National Day of Prayer.

2 – Johnny Nash “I Can See Clearly Now”

3 – Fleet Foxes “Third of May”

4 – John Williams “Imperial Death March”

May the fourth be with you. 

5 – Bob Dylan “Isis”

6 – Thee Oh Sees “Blimp” 

In honor of the Hindenburg disaster.

7 – Al Stewart “You Don’t Even Know Me”

8 – The Four Clefs “V-Day Stomp”

9 – Stevie Wonder “You Haven’t Done Nothin’” 

In honor of the start of Nixon impeachment. 

10 – The Band “The Night They Drove Old Dixie Down”

11 – The Sylvers “High School Dance” 

12 – Alkaline Trio “Donner Party”

Half of these dates could be an Alkaline Trio song about a different murder but let’s go with the Donner Party, somewhat surprisingly not a song about Jeffrey Dahmer. 

13 – The General Strike “Pugon”

14 – Helicopters on Mars “May 14” 

15 – The Quintet “All the Things You Are” 

From the historic Jazz at Massey Hall recording. 

16 – The Beach Boys “God Only Knows”

17 – Bob Dylan “Like a Rolling Stone”

From The Bootleg Series, Vol. 4: Bob Dylan Live 1966, The “Royal Albert Hall” Concert. Related, “Judas!” -some idiot at the show.

18 – Jeen “May 18”

19 – The Who “I’ve Known No War”

20 – Cher “Half-Breed” 

Cher’s birthday deserves to be a national holiday. 

21 – Marvin Gaye “What’s Going On”

22 – The Rascals “A Beautiful Morning” 

23 – Brigitte Bardot and Serge Gainsbourg “Bonnie and Clyde”

A sexy ode to crime. 

24 – DJ Scratch Nice “May 24th”

25 – Wheatus “Teenage Dirtbag”

Does this song reverberate without the mention of prom?

26 – zYklen “May 26” 

27 – Alice Cooper “School’s Out”

My pals and I called our local rock station on the last day of 6th grade to request this song. The Loop played it. 

28 – The Happenings “See You in September”

29 – They Might Be Giants “Istanbul (Not Constantinople)”

The Fall of Constantinople via the best band to ever have a hotline. 

30 – Leonard Cohen “Joan of Arc” 

31 – The Gap Band “You Dropped A Bomb”

June

1 – The Smashing Pumpkins “Rhinoceros”

See you in June. 

2 – The Handsome Family “Drinking Beer on the Roof”

I have lived this song. 

3 – Bobby Gentry “Ode to Billy Joe”

4 – Neil Diamond “Desiree”

5 – Blaze Foley “June or September” 

6 – The Louvin Brothers “Satan Is Real”

For the true believers.

7 – The Everly Brothers “June Is as Cold as December”

8 – Ray Parker Jr. “Ghostbusters”

9 – The Fratellis “Chelsea Dagger” 

The 2010 Blackhawks Stanley Cup Championship turned this into a perennial ear worm.

10 – Yoko Ono “Yes, I’m A Witch” 

The first ‘witch’ hanged in Salem was on June 10. Yoko Ono has been kicking ass for seven decades. 

11 – MJ Lenderman “Hangover Game”

It wasn’t the flu. 

12 – Hugh Masekela “Grazing In The Grass”

13 – Billy Mure “June Is Bustin’ Out All Over”

14 – Jefferson Airplane “Volunteers”

Some people will be happy because it’s a certain POTUS’ birthday. Some will protest. No matter what, things will change. 

15 – Freddie Hubbard “Little Sunflower”

16 – Alan Parsons Project “Sirius”

Your world champion, Chicago Bulls! Well, the first championship in 1991. They won 5 more after that. 

17 – Mitski “First Love/Late Spring”

18 – Depeche Mode “Never Let Me Down Again” 

From the 101 doc/concert film.

19 – P.O.D. “Booyaka 619”

Rey Mysterio! 

20 – The Understones “Here Comes the Summer”

21 – Jeff Rosenstock “June 21st”

22 – The Webb Brothers “Summer People”  

23 – The Fiery Furnaces “Here Comes The Summer”

24 – Roy Ayers Ubiquity “Everybody Loves The Sunshine” 

25 – Ella Fitzgerald and Louis Armstrong “Summertime” 

26 – Fountains of Wayne “It Must Be Summer”

27 – Casa Lomo Orchestra “Happy Days are Here Again”

28 – Fastball “The Way”

A real-life story of an elderly couple that disappeared for weeks and found dead. It’s a great pop song.

29 – Judy Garland “Somewhere Over the Rainbow”

30 – Sly and the Family Stone “Hot Fun in the Summertime”

July

1 – Grandmaster Flash “The Message”

2 – The Who “Summertime Blues”

3 – David Bowie “Rock and Roll Suicide”

Whether eulogizing himself or a version of himself, no one did it better than Bowie.

4 – Woody Guthrie “This Land is Your Land”

Happy Independence Day!

5 – Type O Negative “Summer Breeze” 

6 – Queens of the Stone Age “Feel Good Hit of the Summer”

Duh duh duh – duh duh – duh – duh duh…

7 – Duke Ellington “Festival Junction” 

From the influential Ellington at Newport.

8 – Sleigh Bells “This Summer” 

This sounds and feels like a music festival. 

9 – Fats Waller “Ain’t Misbehavin”

10 – Lee Hazlewood and Nancy Sinatra “Summer Wine” 

11 – Green Day “Jesus of Suburbia”

My favorite Green Day song from their best rock opera (they have two) happens to name drop 7-Eleven. 

12 – The Flying Lizards “Summertime Blues”

13 – Queen “Bohemian Rhapsody” 

The best Live Aid performance. 

14 – Air “Sexy Boy” 

Happy Bastille Day!

15 – Mungo Jerry “In the Summertime”

16 – Billy Bragg and Wilco “Joe DiMaggio Done It Again” 

I can not get a hit on one Major League Baseball pitcher. Joe DiMaggio successfully hit in 56 consecutive games.

17 – “It’s a Small World” 

My favorite Disney song to honor the opening of Disneyland. I loved this song as a kid. I thought it was disturbing as a 20-something. Now in my 40s, it’s somewhere between comfortable and haunting. 

18 – DJ Jazzy Jeff & The Fresh Prince “Summertime” 

Who else watched this music video premiere after a new episode of The Fresh Prince of Bel-Air?

19 – Slim Dusty “When The Rain Tumbles Down in July”

20 – Astrud Gilberto “Fly Me to the Moon”

21 – Big Dipper “Ron Klaus Wrecked His House”

Ron Klaus, did in fact, wreck his house on July 21.

22 – Martha Reeves & The Vandellas “(Love Is Like A) Heat Wave”

23 – Isaac Hayes “Theme from Shaft”

24 – Limp Bizkit “Break Stuff” 

Fred Durst did not cause a riot at Woodstock 99. He didn’t help, but he did not cause a riot. 

25 – The B52’s “Rock Lobster”

26 – Katrina & The Waves “Walking On Sunshine”

27 – The Zombies “Summertime” 

28 – Ramones “Rockaway Beach” 

29 – The Ronettes “Be My Baby”

The recording date of the greatest girl group song of all time.

30 – Wavves “Summer Goth” 

31 – Wendy Rene “BBQ”

August

1 – Harry Nilsson “Rainmaker”

2 – The Sundays “Summertime” 

3 – Rilo Kiley “August” 

4 – Gene Kelly “Singin’ in the Rain”

5 – Misfits “Who Killed Marilyn?”

6 – Orchestral Manoeuvers in the Dark “Enola Gay”

A catch ditty about the atomic bombing of Hiroshima. 

7 – Billie Holiday “Straight Fruit”

8 – The Blues Brothers “Everybody Needs Somebody”

The best live performance of a fictional/real band in a movie about doing the right thing in spite of Nazis and cops. 

9 – Sonic Youth “Death Valley ‘69”

Once again, didn’t try to make this all about death, but the Manson murders still reverberate. 

10 – Khruangbin “August 10”

11 – Rudy Willingham “Pool Party”

12 – Kool & The Gang “Summer Madness”

13 – Nine Inch Nails “Happiness in Slavery”

Nine Inch Nails hated their Woodstock 94 performance but it helped elevate them to stadiums and the performance took home a Grammy.

14 – The Go-Go’s “Vacation”

15 – Automatic “Smog Summer”

16 – Bauhaus “Bela Lugosi Is Dead”

Undead, undead, undead…

17 – Blondie “In the Sun”

18 – Jimi Hendrix “Hey Joe” 

The best performance from Woodstock that isn’t “The National Anthem,” which makes it much more listenable. 

19 – Caviar “Tangerine Speedo”

20 – Urge Overkill “Sister Havana”

21 – Patsy Cline “Crazy”

22 – Portishead “Sour Times”

23 – Connie Francis “Vacation”

24 – Siouxsie and the Banshees “Cities in Dust”

25 – MC5 “Kick Out the Jams”

The 1968 Democratic National Convention theme song.

26 – Pieter de Graaf “August Sings” 

27 – The Champs “Tequila” 

Happy birthday, Paul Reubens!

28 – Mahalia Jackson “How I Got Over”

29 – The Orwells “Last Days in August”

30 – John Prine “Far from Me”

31 – blink-182 “Going Away to College”

I do not miss college. But it was the best of the three education eras. 

September

1 – Deftones “Back to School” (Mini Maggot)”

I do not miss high school. But it was fun. 

2 – The White Stripes “We’re Going to Be Friends”

I also do not miss grade school. But it was pleasant. 

3 – The Temptations “Papa Was a Rolling Stone”

4 – The Beatles “Blackbird”

5 – Barry White “September When I First Met You”

6 – Big Star “September Gurls”

7 – Shannon Shaw “Goodbye Summer” 

8 – The Decembrists “When The War Came” 

The Decembrists have multiple songs about historic events but this one about the Siege of Leningrad is my favorite. 

9 – Nation of Language “September Again”

10 – BB King “Every Day I Have the Blues” 

From his Cook County Jail live album. The late 60s and early 70s were a good time to see blues legends and country legends if you were behind bars?

11 – Wilco “Jesus, etc.”

The best song about 9/11 written before 9/11.

12 – Tony Bennet “Maybe September”

13 – Deodato “September 13”

14 – Madonna “Like a Virgin”

The best MTV Video Music Awards performance. Or at least most iconic.

15 – Glenn Miller “In The Mood”

16 – Frazey Ford “September Fields”

17 – Hank Williams “Your Cheatin’ Heart”

18 – Type O Negative “September Sun”

19 – OutKast “B.O.B”

The best OutKast song that has nothing to do with the 19 September 2010 Baghdad bombings but it feels somewhat related. 

20 – Mickey and the Soul Generation “Football” 

This instrumental has an early fall vibe.

21 – Earth, Wind & Fire “September”

Maybe the most obvious choice on this entire calendar. 

22 – My Morning Jacket “Old September Blues”

23 – Frank Sinatra “September Song”

24 – Fiona Apple “Pale September”

25 – Hank Williams “All My Rowdy Friends Are Coming Over Tonight” 

This song is appropriate most days from September through December. It’s the September 25 pick since it’s the most emotional Monday Night Football game, the first game in the Superdome post Katrina.

26 – Willie Nelson “September Song”

27 – Agnes Obel “September Song” 

28 – Rod Stewart “Maggie May”

29 – Badfinger “Baby Blue”

The Breaking Bad finale is damn near perfect.

30 – Green Day “Wake Me Up When September Ends”

Wake up. 

October

1 – Ministry “Every Day is Halloween” 

Welcome to Spooky Season!

2 – Broken Bells “October”  

3 – Sinead O’Connor “War”

The most important protest performance in Saturday Night Live history. 

4 – R.E.M. “What’s The Frequency Kenneth?”

I did know this was about an attack on newscaster Dan Rather until this project. R.E.M. has to be the band with the most hits about the most interesting and odd people and events. How was this a hit?!?

5 – Woody Herman “Early Autumn”

6 – The Ink Spots “Shine On Harvest Moon”

7 – Steve Conway “October Twilight” 

8 – Iron & Wine “Autumn Town Leaves”

Dude sounds like the fall. 

9 – Bad Bunny “Mr. October” 

Reggie Jackson should be honored.

10 – Yo La Tengo “Autumn Sweater”

The sonic equivalent of a comfy autumn sweater. 

11 – Coleman Hawkins “Body and Soul”

12 – The Kinks “Autumn Almanac”

13 – The Gaslight Anthem “Autumn”

14 – Serengeti “Don’t Blame Steve”

Steve Bartman did not collapse the 2003 Chicago Cubs.

15 – Lee Hazlewood “Johnny October”

16 – Ghost Country “October Country”

17 – October Country “October Country”

18 – Okonski “October” 

The song that inspired this project, this 2025 Okonski song is one of the best tracks of last year.

19 – Felsmann + Tiley “October” 

20 – Neil Diamond “Sweet Caroline” 

The Boston Red Sox victory over the New York Yankees in the 2024 ALCS is the most important championship series game in the modern era. Curses end. 

21 – The White Stripes “Dead Leaves and the Dirty Ground”

The White Stripes are canonically a fall band.

22 – Led Zeppelin “Ramble On”

23 – Journey “Don’t Stop Believin’”

The 2005 Chicago White Sox postseason run featured the future first Chicago president throwing out a first pitcg and the future first Chicago pope sitting in the stands. The team’s unofficial theme song that year was a Journey song about never giving up. It’s here because October 23, 2005 was the date of the last White Sox World Series home game. They swept the Houston Astros. Sox win. Chicago President wins. Chicago Pope wins.

24 – Dennis Coffey & The Detroit Guitar Band “Scorpio”

It’s Scorpio season. 

25 – The Undertones “Teenage Kicks” 

John Peel, one of the most important DJs, died October 25. His gravestone features a lyric from this song. It’s a perfect song.

26 – Kurtis Blow “Basketball” 

The date of the start of the 1984 NBA season, the year of this song’s release.

27 – Percy Sledge “Spooky”

Soul music oddly has the best Halloween music. 

28 – Otis Redding “Trick or Treat”

See above. 

29 – Bobby “Boris” Pickett “Monster Mash”

Respect the anthem.  

30 – Ringo Starr “Snookeroo”

31 – John Carpenter “Halloween Theme”

John Carpenter owns Halloween. That’s why the official title card of the film says, “John Carpenter’s Halloween.” 

November 

1 – Gorillaz, MF Doom “November Has Come”

2 – The Mountain Goats “Cubs In Five”

“And I will love you again.”

3 – Steve Goodman “A Dying Cubs Fan’s Last Request”

The 2016 Chicago Cubs did it.

4 – New Edition “Candy Girl” 

In honor of National Candy Day.

5 – John Lennon “Remember”

6 – Wyclef Jean “Gone Till November” 

7 – Radiohead “Electioneering”

8 – Trent Reznor and Atticus Ross “Election Night-mare”

9 – Tom Waits “November”

10 – Gordon Lightfoot “The Wreck of the Edmund Fitzgerald”

Ships sink. 

11 – Wednesday “November” 

12 – The National “Mr. November” 

13 – Lee Hazlewood and Nancy Sinatra “(L’ete Summer) Indian Summer”

14 – SZA “Sweet November” 

15 – John Lennon and Yoko Ono “Give Peace A Chance” 

Performed in Washington at the Moratorium to End the War in Vietnam on November 15, 1969.

16 – Edith Piaf “Autumn Leaves”

17 – Cannonball Adderly “Autumn Leaves”

18 – Nirvana “Where Did You Sleep Last Night” 

The best song from the best Unplugged.

19 – Guns N’ Roses “November Rain” 

20 – Sturgill Simpson “Mercury in Retrograde”

21 – Television “Marquee Moon” 

World Television Day exists as an excuse to listen to Television.

22 – The Rolling Stones “Sympathy For The Devil”

Who killed the Kennedys?

23 – Green Day “Macy’s Day Parade”

The date of the Macy’s Day Parade the year Green Day’s Warning was released.

24 – Thelonius Monk “Stuffy Turkey”

The second selection in our week of Thanksgiving adjacent songs.

25 – Jay & The Techniques “Apples, Peaches, Pumpkin Pie”

See above.

26 – Adam Sandler “The Thanksgiving Song”

Love to eat turkey…

27 – Vince Guaraldi Trio “Thanksgiving Theme”

Love to eat popcorn…

28 – Drive-By Truckers “The Thanksgiving Filter”

A modern portrait of Thanksgiving.

29 – Morrissey “November Spawned a Monster”

30 – Ice Cube “It Was a Good Day”

The day was November 30. 

December

1 – Collective Soul “December” 

An undeniably catchy riff. I am ashamed to enjoy this song.

2 – Norah Jones “December”

3 – Elvis Presley “If I Can Dream” 

A hopeful plea from the 68 comeback special.

4 – Jay-Z “December 4th”

Not a lot of songs mention the artist’s inception.

5 – The Replacements “Here Comes a Regular” 

National Bartender Day had to have a Replacements song.

6 – Static X “December”

7 – Mazzy Star “Flowers in December”

8 – Teenage Fanclub “December” 

9 – Counting Crows “A Long December”

The best song in their catalog, a tune so good a performer in a piano bar may get you to tear up. 

10 – Julian Doiron “Will You Still Love Me In December”

11 – Lester Flatt and Earl Scruggs “Foggy Mountain Breakdown”

12 – Cake “Frank Sinatra” 

Sinatra’s birthday

13 – Talking Heads “Psycho Killer” 

The opening performance from the groundbreaking Stop Making Sense.

14 – The Monkees “Circle Sky”

Watch Head and listen to the soundtrack of Head on World Monkey Day.

15 – Elvis Costello “Radio, Radio”

A great SNL performance that was misunderstood at the time and continues to be misunderstood. 

16 – Boney M. “Rasputin”

17 – Sugar Ray “Fly” 

The Wright Brothers flew so Sugar Ray could fly.

18 – Open Mike Eagle “The Black Mirror Episode”

The only song on this list about a television show inspiring a real life divorce. While Open Mike Eagle won’t disclose which episode it is, most of Reddit thinks it’s “The Entire History of You,” the season 1 finale that originally aired December 18, 2011. 

19 – The Four Seasons “December, 1963” 

20 – Tom Petty and the Heartbreakers “Christmas All Over Again”

A song about an adult man that likes his extended family enough to be happy to see them at Christmas but glad he doesn’t see them everyday. Also, he asks for a Rickenbacker guitar.

21 – Soundgarden “Fell on Black Days” 

On the darkest day of the year.

22 – Merle Haggard “If We Make It Through December” –

23 – Miles Davis “On Green Dolphin Street” 

From Miles Davis’ The Complete Live at the Plugged Nickel 1965. 

24 – The Pogues “Fairytale of New York”

25 – Elvis Presley “Blue Christmas”

26 – Ben Folds Five “Brick” 

Happy day after Christmas!

27 – Cap’n Jazz “Winter Wonderland”

28 – Caveman “December 28th”

29 – Cake “The Winter”

30 – Ella Fitzgerald “What Are You Doing New Year’s Eve?” 

31 – Alkaline Trio “Private Eye”

It was this or “Auld Lang Syne” but that song doesn’t name check Channel 11, Chicago’s PBS station.

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