The Bracket of Me

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By: Connor Lenahan

Lists and Brackets. These are two things I cannot get enough of. I can’t quite place my finger on it, but I think I might know why. Its a way of organized discussion to determine the best of something. Whenever someone asks me what my “favorite movie” or “favorite show” is I will inevitable have to give a list. I consciously rank things to keep track of what I deem the “best” of something.

I love the bracket idea because it allows for a tournament – always fun – and for me to challenge my own brain to make tough decisions. I will do random tournaments for fun. This is one of them.

Shockingly, the only bracket I’ve published previously is “The Tournament of The Dan,” determining the best Steely Dan song of all time last July. I also announced just last night that my masterwork, a 512 episode bracket of episodes of The Simpsons is coming soon.

So what is this monstrosity above? It’s a completely insane way of determining what I consider my favorite song of all time. It is entirely crazy and basically doesn’t make sense, as bands like Alabama 3 make it over Fiona Apple. Here’s how I did this. I took the most played songs in my iTunes. The highest played song was “Black Skinhead” by Kanye West, which makes West the #1 seed overall. I then chose my favorite West song, “Runaway,” to represent him. I then went to the highest played song by someone else, “Favorite Song,” by Chance the Rapper and Childish Gambino, and that became the #2 seed representing Chance. I’d continue to go to the next highest played artist and pick a song to represent them until I fielded a 64 song bracket. Did you get all that? Me either.

At the very least this will be a peak into my musical tastes which legitimately make no sense.

Lets’s go.


Northwest Region – Round 1

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#1 “Runaway” – Kanye West vs #16 “Get Ur Freak On” – Missy Elliot

Okay there is no question in my mind who wins this matchup, but can we just take a second to remember how great Missy Elliot is? It’s sad that she hasn’t had a new album since 2006. She really made some classics, especially “Get Ur Freak On.” But sadly that’s gone for Kanye’s Magnum Opus.

#2 “All My Friends” – LCD Soundsystem vs #15 “Ignition Remix” – R Kelly

I’m about to commit an act of treason against the United States by knocking out “Ignition,” but it has to be done. While it is the epitome of “party” and “classic,” it isn’t nearly the beautiful, perpetually building longing for a life removed that James Murphy gives the world in “All My Friends.” Sorry R.

#3 “Banana Clipper” – Run The Jewels vs #14 “Wake Up Alone” – Amy Winehouse

I will always have a soft spot in my heart for Killer Mike of Run The Jewels after he was not only kind to me backstage at Governor’s Ball, but also after he put me on his Instagram (it’s there, look it up). The Run The Jewels album is one of the most fun listens I’ve ever had, but it sadly pales in comparison to the 10 song masterpiece that is Back to Black. I was sad the day Amy Winehouse died and I’m still sad now. “Wake Up Alone” is beautiful. It’s the song off Back to Black that makes me angriest that she will never release anything else.

#4 “Harder To Breathe” – Maroon 5 vs #13 “Runaway Baby” – Bruno Mars

Songs About Jane starts with “Harder To Breathe” and immediately becomes one of the best albums of the 2000s. I challenge you to disagree with me there. Peace, Bruno.

#5 “Public Service Announcement” – Jay Z vs #12 “What Goes Around Comes Around” – Justin Timberlake

I hate everything. I hate everyone. This is like being asked which of your children lives and which dies. This is awful. I hate everyone. Why God, why?

“PSA” is the only rap song that I have ever successfully rapped all of of the top of my head without any music playing. It’s my favorite Jay Z song and seeing it live with my friend Montana Rispoli remains one of the best moments of my life. It’s gotta go through. I love you Justin. I always will.

#6 “Higher Ground” – TNGHT vs #11 “Yeah!” – Usher

Fact: TNGHT’s Hudson Mohawke is a genius. Fact: “Yeah!” is probably the greatest dance track in history. We’re done here.

#7 “Big Spender” – Theophilius London/A$AP Rocky vs #10 “It’ll All Work Out” – Blake Mills/Fiona Apple

“Big Spender” is a fun song, but I cannot even begin to fathom putting it into the same category of song that “It’ll All Work Out” is in in my brain. I heard the song for the first time when I saw Fiona Apple last October. It’s as haunting yet amazing today as it was that night.

#8 “Take Me Out” – Franz Ferdinand vs #9 “Only” – Nine Inch Nails

“Take Me Out” has one of the 15 best guitar riffs of any song in the past two decades. No contest.

Round 2

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#1 “Runaway” vs #8 “Take Me Out”

I give my apologies to the Scottish rockers of the latter song, for in another bracket section they would have faired much better. Sadly they happened to run into the proverbial Grizzly Bear with Chainsaw Arms of this tournament in “Runaway.” Yeezus takes no prisoners.

#2 “All My Friends” vs #10 “It’ll All Work Out”

True story, James Murphy’s closing “If I could see all my friends tonight” was the final thing I heard in my car when I parked in my driveway the night before I moved to Boston. I still get chills thinking about that moment. It all became real that second that I was moving away. Yeah, that song means a lot to me. I think that’s pretty much a clear cut win.

#4 “Harder To Breathe” vs #5 PSA

Whenever I hear the first second of “PSA” I put my hands together in the diamond. “Allow me to reintroduce myself my name is HOV” causes me to throw said diamond skyward and lose all control of my emotions. “Harder To Breathe” reminds me of 2003. Game, set, match, Hova.

#6 “Yeah!” vs #10 “Wake Up Alone”

This was actually pretty close, but I’m giving the nod to “Yeah!” which was my favorite song from 2004 to at least 2007.

Round 3

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#1 “Runaway” vs #5 “PSA”

Do I want to be shot in the left side of my head or my right? Dammit this is hard. Why do I do these things to myself?

Here’s my quick reasoning. In 2010, thanks to “Runaway,” Kanye West completely transformed my perception of him and his music. He has since become one of my three favorite artists ever. Jay Z gradually won me over, but “PSA” was one of many that did so. Direct responsibility gives it it Kanye.

#2 “All My Friends” vs #6 “Yeah!”

Usher will always be in my heart. But his time has come. The hammering piano intro to “All My Friends” builds for the entirety of the song to the need to return to a life surrounded by friends creating this beautiful movement of music. LCD storms through.

Round 4

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#1 “Runaway” vs #2 “All My Friends”

For one of the most wonderfully delusional people in human history to have a moment of beautiful self-awareness – a realization of all the shit he has put people through – and tell people that maybe he isn’t worth the trouble he causes is one of the most heartbreaking yet genius things I’ve ever witnessed. Kanye hits that on “Runaway.” It’s a flawless song.

Southwest Region – Round 1

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#1 “Little Sister” – Queens of the Stone Age vs #16 “Tighten Up” – Black Keys

There is a rule in this universe that we all must follow. That rule is that when faced with the decision “Cowbell of Whistling” you must always choose the former. Cowbell is life. “Little Sister” is awesome.

#2 “Too Much” – Drake vs #15 “Grindin'”- Clipse

I’m still speechless about hearing “Too Much” for the first time last fall. I remember being blown away by how emotionally honest it was. Not just in reminiscing about Drake’s own beginnings to his career, but also his family. It was real. In a world of personas, he was a person. “Too Much” remains a highlight of Drake’s career.

#3 “Da Mystery of Chessboxin'” – Wu-Tang Clan vs #14 “Nosetalgia” – Pusha T/Kendrick Lamar

Here’s the reason why Wu-Tang wins. “Represent the GZA, Abbot, RZA, Shaquan, Inspectah Deck Dirty Ol’ getting low wit his flow
Introducing, the Ghost..face.. Killah!!”

That may be my favorite line in rap history. And for those of you who have no idea why it stands out (2:24):

#4 “Problem” – Ariana Grande/Iggy Azalea vs #13 “The Way I Are” – Timbaland/Keri Hilson

I love Ariana Grande as much as the next red-blooded American male, but can we all agree that “The Way I Are” should be on the playlist for every party for the remainder of history? If you disagree you are wrong and should be deported.

#5 “Ain’t It Fun” – Paramore vs #12 “Thrift Shop” – Macklemore

Lol Macklemore. Yeah, that was funny. Let’s go Paramore.

#6 “Switch” – Will Smith vs #11 “Play The Guitar” – B.o.B/Andre 3000

It is impossible to say the word “squiggle” or “bubble” and be angry. It is similarly impossible to listen to “Switch” and be upset. You could get mugged and still bust a move when the hand claps start for “Switch.” It’s incredible.

#7 “Talk Dirty” – Jason Derulo vs #10 “Sweater Weather” – The Neighbourhood

All credit for me finding “Sweater Weather” goes to my brother Chase, who recommended it or played it in the car once last winter. It’s been stuck in my head ever since. That chorus is just hypnotizing. Also, as pointed out to me by Elyse Notarianni, “Talk Dirty” is awful once you hear the vastly superior Spanish version.

#8 “1 Thing” – Amerie vs #9 “Kid Charlemagne” – Steely Dan

Is there gas in the car? Yes there’s gas in the car. Steely Dan all day every day.

Round 2

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#1 “Little Sister” vs #9 “Kid Charlemagne”

Look I love Queens of the Stone Age and all, but they don’t even enter the same county as Steely Dan in this conversation. Ballads of LSD Chefs win forever.

#2 “Too Much” vs #10 “Sweater Weather”

Every single time “Too Much” comes on I stop what I’m doing. It shuts me down. It’s crazy powerful. That’s a special song.

#3 “Da Mystery of Chessboxin'” vs #6 “Switch”

More and more “Switch” has become my happy song. It’s a sign that all is right with the world. It is also key to go crazy and have fun. How can you not love this song?

#5 “Ain’t It Fun” vs #13 “The Way I Are”

“Ain’t It Fun” is an incredible song. If the only voice you heard from it was that of Haley Williams then the track would be one of the best Paramore has ever made. The choir backing her voice elevates everything. It makes this into one of the best songs I’ve ever heard. Plus, “don’t go crying to your mama, cause you’re on your own in the real world,” is one of the most brilliant lines in music.

Round 3

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#2 “Too Much” vs #6 “Switch”

These two songs cause two polar opposite reactions for me. “Too Much” shuts me down while “Switch” fires me up. It’s a razor thin margin, but I’m giving the nod to “Switch.” I like living life, and that’s what I want to do when I hear “Switch.”

#5 “Ain’t It Fun” vs #9 “Kid Charlemagne

I’m not sure how, but Donald Fagen and Walter Becker made a story of a drug dealing outlaw hilarious. Seriously, more than ten years later I still laugh at “Is there gas in the car?” like I did in my dad’s car the first time I heard it. Actually, because I can clearly remember the first time I heard this song, I think I need to go with Steely Dan.

Round 4

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#6 “Switch” vs #9 “Kid Charlemagne”

Shocker: Steely Dan is my favorite band of all time. After all, I did write a 5000 song bracket dedicated to their music. They have made a gargantuan impact on my life. This fall I’m going to see them for a fifth time. When they fire up “Kid Charlemagne” I will stand up and sing every word. It’s part of who I am.

Northeast Region – Round 1

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#1 “Favorite Song” – Chance The Rapper/Childish Gambino vs #16 “Brand New Day” – Sting

“Favorite Song” was introduced to me last fall by my friend Jason Kohn. Ever since it has been playing on my iPod constantly. It has become, more or less, the song of my summer in 2014. The only problem for it is that I have loved the song “Brand New Day” since I saw Sting in concert in 2001. That’s right, I saw Sting live when I was seven years old. And he was terrific. “Brand New Day” exceptional. Upset of the day, Sting goes on.

#2 “Blackbird” – Alter Bridge vs #15 “Antidote” – Swedish House Mafia

We are going to have a lot of time to talk about Alter Bridge. Quick shoutout to Swedish House Mafia, but this isn’t your day.

#3 “Reptilia” – The Strokes vs #14 “Turn Down For What” – Lil Jon

While I made clear on Twitter recently that “Turn Down For What” is better than any song Bob Dylan ever wrote (and quite possibly lost a follower in the process) I cannot in good conscience send it past Julian Casablancas and Co. “Reptilia” is too good. Thanks to Matt Bruzzano for showing me it way back when.

#4 “Pepe Lopez” – Action Bronson vs #13 “Ready to Start” – Arcade Fire

While “Pepe Lopez” is hilarious, it’s just Bronson rapping over the song “Tequila,” it’s simply not as good of a song as “Ready to Start” is. That was the first song by Arcade Fire I ever heard and still my favorite.

#5 “Retrograde” – James Blake vs #12 “Live Fast, Die Young” – Rick Ross/Kanye West

I wrote about “Retrograde” with one of my first articles of 2014. I still think it is a beautiful song. I also happen to have “Live Fast, Die Young” as not only one of my favorite Kanye beats ever made (seriously, he produced this song) but one of my favorite Kanye verses as well. Another upset here. Rozay and Yeezy advance.

#6 “She Knows” – J Cole vs #11 “Goldie” – A$AP Rocky

I happen to love both of these songs. I needed a tie breaker because I couldn’t find a reason as to why I’d pick one over the other. I’m not hyper passionate about wither, but I love them. My tiebreaker was that I am unable to sing along to “She Knows” as I don’t know all the words. I might be able to rap all of “Goldie” off the top of my head. That told me what I needed to know.

#7 “House Party” – Meek Mill vs #10 “Untitled (How Does It Feel)” – D’Angelo

Fun fact: Meek Mill has two volumes – screaming and not talking. While this makes for a great song to get pumped up to it can also give you a headache. Meanwhile “How Does It Feel” is the epitome of what Ron Burgundy would call “baby making music.” I love it too much to let it leave. Thanks for yelling Meek.

#8 “Shabba” – A$AP Ferg/A$AP Rocky vs #9 “Pretty Thing” – Bo Diddley

In the very likely case you don’t know what song “Pretty Thing” is, it’s the track playing when Leonardo DiCaprio dances at his wedding in The Wolf of Wall Street. That scene made me laugh hard enough that “Pretty Thing” was in rotation for a few months. Alas, Ferg and Rocky absolutely murder the “Shabba” beat and advance here.

Round 2

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#2 “Blackbird” vs #10 “How Does It Feel”

Yesterday I was trading songs with my friend Laura LaBrecque when I needed to pick one of my all time favorites. This was going to be a representation of my musical tastes. What did I choose? “Blackbird.” That’s saying something. I’ll always love you D’Angelo

#3 “Reptilia” vs #11 “Goldie”

“The room is on fire while she fixes her hair” gets me every single time. That is pure gold. I lose it. I love “Reptilia.” Thanks Rocky.

#8 “Shabba” vs #16 “Brand New Day”

When you come back to a song for the first time in years it’s a magical moment. You fall in love again. Sometimes, if you’re lucky, you’ll remember the words to the song. I remembered every word to “Brand New Day” after going years without listening to it. That song just sticks with me.

#12 “Live Fast, Die Young” vs #13 “Ready To Start” 

Yeah this is pretty much a no contest in Kanye’s favor.

Round 3

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#2 “Blackbird” vs #3 Reptilia

“Blackbird” came out seven years ago. That is a lot of time I spent listening to music and discovering thousands of new songs. Through all that time I stood by one belief, that the guitar solo played by both Myles Kennedy and Mark Tremonti was the best I have ever heard. It still is today. It’s going to be tough to take this one down.

#12 “Live Fast, Die Young” vs #16 “Brand New Day”

The album version of “Brand New Day” is pretty good. But that’s not the one I ever listen to. No, I go for the live version from 2001’s All This Time live album, recorder the evening of 9/11. It hits me like a sledgehammer every time I listen of how powerful this performance was on such a tough night. But the message was there, tomorrow is a new day. It’s really a special song.

Round 4

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#2 “Blackbird” vs #16 “Brand New Day”

When I saw Alter Bridge a few months ago the only song I cared about seeing was “Blackbird.” I had waited seven years to hear Myles Kennedy belt out the song dedicated to a friend of his that had passed. When I heard it I knew in that moment that it was perfect. That was a central point to my childhood and one of my favorite songs for an almost decade. As much as I love “Brand New Day” it just doesn’t have the power that “Blackbird” maintains each listen.

Southeast Region – Round 1

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#1 “Rosa Parks” – OutKast vs #16 “Wolf Like Me” – TV On The Radio

One of the toughest parts of this bracket was picking which song I’d put in for OutKast. There were a bunch of candidates. The truth is that most if not all of them would have beaten “Wolf Like Me” like “Rosa Parks” does.

#2 “Heartbeat” – Childish Gambino vs #15 “Freakum Dress” – Beyonce

Yes, my favorite Beyonce song is really “Freakum Dress.” And yes, I did just knock Beyonce out in the first round. Come at me.

#3 “I Bet You Look Good On The Dancefloor” – Arctic Monkeys vs #14 “Oblivion” – Grimes

High energy, danceable, British, insane guitar work – give me a reason not to love Arctic Monkeys.

#4 “Hot In Herre” – Nelly vs #13 “Dip” – Danny Brown

One of my favorite articles I’ve ever written was about when a San Francisco radio station played “Hot In Herre” for four straight days. I listened to that station for over two hours listening to Nelly. It was flawless. God Bless America.

#5 “Backseat Freestyle” – Kendrick Lamar vs #12 “Holocene” – Bon Iver

“Backseat Freestyle” was the first time I realized that Kendrick Lamar was absurdly talented. The more time I’ve spent with the song the more I realize how gifted he is. No on, read: no one, makes that song other than him. It’s incredible. I love “Holocene,” but my real favorite Bon Iver song is “Lost In The World,” which happens to be a Kanye West song. Rules are rules, Kendrick goes on.

#6 “Fancy” – Iggy Azalea/Charlie XCX vs #11 “Collard Greens” – Schoolboy Q/Kendrick Lamar

I remember my buddy Eric Fanning putting on Collard Greens while we were cleaning up his suite one night and him starting to dance to the track. Now, reflexively, I too dance to “Collard Greens” like our 6’5″ small forward. This might be embarrassing when I begin to dougie in a supermarket, but it’s so much fun.

#7 “212” – Azalea Banks vs #10 “Bad Religion” – Frank Ocean

“212” is great, but “Bad Religion” is “Bad Religion.” If you aren’t sobbing at the end of it then you are heartless. Frank marches on. Thanks to Celine Brunetti for showing me “212.”

#8 “Woke Up This Morning (Sopranos Theme)” – Alabama 3 vs #9 “Blurred Lines” – Robin Thicke/TI

Two things Robin Thicke will not be getting: 1. Paula Patton back, and 2. Into Round 2.

Round 2

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#1 “Rosa Parks” vs #8 “Woke Up This Morning”

I found out a few months ago that “Woke Up This Morning” is a whole lot better than you’d imagine given that it’s a TV theme song. It’s actually an awesome song to set the mood for a huge sporting event, which is exactly how I used it last year for basketball. But when I needed to get excited about the Seahawks running away with the Super Bowl I turned to “Rosa Parks” and started dancing for hours. It’s a special song.

#2 “Heartbeat” vs #10 “Bad Religion”

This is weird. Even though Childish Gambino is one of my absolute favorite artists alive, he just happened to hit bad luck early twice. While “Heartbeat” is incredible, it cannot match up to Frank Ocean ripping himself open and showing you his heart. I love you Donald.

#3 “I Bet You Look Good On The Dancefloor” vs #11 “Collard Greens”

When my brother Cary got to meet Alex Turner in the lobby of our hotel in Dublin it was entirely no fair. When he told me that he did I almost punched him in the face. I think that means Arctic Monkeys should go on.

#4 “Hot In Herre” vs #5 Backseat Freestyle

Okay the narrowest of margins falls Nelly’s way here only because “Hot In Herre” is a singular classic whereas “Backseat Freestyle” is  a single classic surrounded by other songs of equal quality on good kid m.A.A.d city. Plus “Hot In Herre” is the catchiest thing ever.

Round 3

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#1 “Rosa Parks” vs #4 “Hot In Herre”

One word: Hoedown. The breakdown in “Rosa Parks” into a hoedown led by the greatest harmonica this side of Stevie Wonder makes me jump up and go crazy every single time it comes on. While “Hot In Herre” is flawless it falls to an even more flawless song in “Rosa Parks.”

#3 “I Bet You Look Good On The Dancefloor” vs #10 “Bad Religion”

“This unrequited love, to me it’s like a one man cult.” Tears. So many tears. I can’t stop crying.

Round 4

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#1 “Rosa Parks” vs #10 “Bad Religion”

I am more emotionally moved by “Bad Religion” than just about every other song I’ve ever heard. I also happen to connect “Rosa Parks” with some of the happiest memories I have ever had. I am an optimist by nature, so I make the judgment call to go with “Rosa Parks,” while still maintaining that I want to give Frank Ocean a hug every time I hear “Bad Religion.

Final Four

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#1 “Runaway” vs #9 “Kid Charlemagne”

I have been thinking how to make this decision for hours now. I think I finally figured it out. When I made the Steely Dan bracket last year I had “Kid Charlemagne” in the final two. It ended up losing there to “My Old School,” which a year later I still believe is the best song that Steely Dan ever made. “Kid Charlemagne” just happens to be my favorite. But I’m going “Runaway” for almost that exact reason. I think it is not just my favorite Kanye West song by a mile, which it is, but I also think it’s the best song he’s ever made. It was a peek behind the curtain at Oz. It’s when Kanye stopped being Kanye West and was finally Kanye West. He was human. And it was perfect.

#2 “Blackbird” vs #1 “Rosa Parks”

“Rosa Parks” is one of my absolute favorite songs ever, but this is actually an easy choice to make against them. “Blackbird” has been etched in stone atop the list of my favorite songs for the seven years it has existed. It’s almost like a symphony. I have never heard guitar work like that of Myles Kennedy and Mark Tremonti before or since. I haven’t heard a vocal performance like Kennedy’s ever. He hits inhuman notes on that song. It’s a masterpiece. It’s one of my favorite pieces of written work ever.


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#1 “Runaway” vs #2 “Blackbird”

In the end, I knew what it had to be. While “Blackbird” remains a beautiful, amazing, perfect creation, it is just that – a creation. It’s a construction made by the band as this unbelievable work. But “Runaway” is real. It’s a person, admitting faults, apologizing for actions, and warning those to stay away for he’s nothing but trouble. Kanye West is a gigantic influence on me, only in the best possible ways, and this song is what showed me that he was and is a genius. As someone who appreciates honesty and emotional openness over anything else, “Runaway” speaks to my soul. That’s why it wins for me.

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Here’s how the entire tournament panned out.

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Thank you for reading, and hopefully now you have a better look into my psychotic musical mind.

– Connor