Chris Legends 2023

1. “Long Time”, “Game Theory”, & “The Seed (2.0)” — The Roots.

The Roots have to kick off my Legends playlist for 2023, no question. Quest Love (The Roots’ drummer) himself is a Black icon of music, and The Roots as a group are incredible. Real, complex, dynamic instrumentals. Intelligent, powerful, thoughtful lyrics. And just so many great songs; it was hard to nail down three for this list.

I chose “Long Time” because it’s my all-time favourite song of theirs; so summer, so chill, so funky, and so tight in terms of lyrics. I chose “The Seed 2.0” because that for me represents The Roots’ ability to make catchy hit records, while still keeping them soulful and — as Diddy says — “Black as a m*therf*cker”. And I chose “Game Theory” because it when it kicks in at 0:56 it is one of the most kick-through-the-door hiphop songs of all time.

When I saw them live that year (’07), they opened the show by walking through the crowd, from the back of the venue, rapping and playing that song. People went wild. One of the all time great groups in hiphop, and to quote myself — even Jimmy Fallon can’t make these guys uncool. ;)

Live version: even funkier.

2. “Respect”, “I Say A Little Prayer”, & “(You Make Me Feel Like) A Natural Woman” — Aretha Franklin

What can you write about Aretha that doesn’t sound like an understatement about how incredible she is? The Queen of Soul — whose career is charted by many as the greatest artist of all time. Civil Rights activist — a close friend of Martin Luther King Jr., a staunch advocate for Black rights, Women’s rights, and Indigenous rights, and a committed fundraiser, known to cover payroll for civil rights organizations. The first woman to be inducted into the Rock and Roll Hall of Fame, who flipped Otis Redding’s “Respect” on its ear to make it both a feminist anthem and one of the most recognizable hits of all time.

Even writing the above sounds flat compared to the legendary arc of her life and career; kind of like me singing along to Respect in the car. But hey, I tried. I chose “I Say A Little Prayer” because her voice on that melody is one of my all-time favorites (it’s also so powerful it makes you forget that the chorus is in 11/4 time signature, which also underscores her mastery of music and composition), and “(You Make Me Feel Like) A Natural Woman” because it’s one of the most soulful songs ever written and sung, in my opinion, and the kind of songs that even an alien species could stumble on and think to themselves “Well… maybe those humans aren’t so bad after all!” “Freedom” sadly isn’t on Spotify, but that has to be an honourable mention, along with “Chain of Fools” and “Since You’ve Been Gone”.

Also if you love the music on these, check out the documentary Muscle Shoals which tells the amazing story of the small southern FAME and Muscle Shoals studio and the session musicians — most of them white — who were up there with the Funk Brothers of Motown. An amazing story, and they played some pretty nice tunes on Franklin’s hits, among many others!

3. “Rosa Parks” & “Bombs Over Baghdad” — Outkast

Outkast is truly in their own lane, where talent, message, and style are concerned. The funky duo from the ATL, known for offering two-word Grammy acceptance speeches such as “Stank You”, who aren’t afraid to play with different genres, and reinvent themselves, are without question, Black legends of music.

“Rosa Parks”, to me, is one of those perfect hiphop songs. It’s also so country, in an Outkast-ATL way. Andre’s verse is one of my all-time favorite verses ever:

“But / anyhow / when in doubt, / went on out and bought it
’Cause I thought it would be jammin’, / but examine / all the flawsky-/wasky
Awfully / sad and it’s costly / but that’s all she / wrote
And I hope I never have to float / in that boat /
Up sh*t’s creek / “It’s weak” / is the last quote
That I wanna hear when I’m goin’ down / when all’s said and done
And we got a new Joe in town /
When the record player get to skippin’ and slowin’ down /
All y’all can say is them n*ggas earned that crown / but until then

Big Boi’s verse is amazing too but that rhyming, flow, creativity and the thinking outside the box is André 3000 to a T.

And I picked “Bombs Over Baghdad” because not only is it an incredible display of lyrical prowess at high speeds, but it was also the song they opened for when they reunited at Coachella after being broken up for 10 years. It was such a beautiful, epic moment to be there for that. Night one, headliner, sunset had just gone down, and the stage was pitch black and then the intro to this song played twice and the crowd went apesh*t and everybody screamed the “One… Two… One, Two, Three, YEAH Inter-national/ underground thunder pounds when I stomp the ground / WOO” You know the rest.

4. “Thriller” & “Circle of Life” — Oren, Maxine and Julia Waters

This legends pick is thanks to the amazing documentary 20 Feet From Stardom, which profiles the Oren, Maxine and Julia Waters, and the amazing career that these three have had.

They have been part of over 260 gold and 100 platinum albums, and have sung backup for legends such as Don Henley, Neil Diamond, Paul Simon, and have also provided actual creature noises on movies like “Avatar”. But my two picks have to be “Circle of Life” from The Lion King soundtrack, and “Thriller”, the title track of one of the most famous and critically acclaimed albums of all time. For their amazing singing abilities, these unsung heroes of Black music history are on my legends list. And definitely watch “20 Feet From Stardom” — just to see their interview is worth it!

5. “I’m Coming Home”, “Bad Boy For Life”, & “I’ll Be Missing You” — Diddy

The flashy style, goofy dance moves, and the frequent name changes have made Diddy an easy “love to hate” figure for some, but in my opinion, Sean Combs is without question a legend in Black music history, and music history in general, in my opinion.

Diddy grew up in Harlem, New York, and by all accounts, did not have an easy upbringing. Working for the drug kingpin Frank Lucas (portrayed by Denzel Washington in American Gangster), his father was shot and killed when Diddy was three years old, which had a marked effect on Diddy’s life, pushing him to stay “off the streets”, study in school, and seek out legitimate business. He entered the music industry first as an intern, then as a promoter, and finally founded Bad Boy Records, which would reinvigorate New York’s dominance over hiphop by breaking acts like Mase, Lil’ Kim, and of course the prolific Notorious BIG.

Diddy has reinvented himself time and time again over the years, has translated his success into other industries, and was one of the first major Black celebrities I noticed to consistently push the phrase “Black Excellence”.

But for me, it’s his messages, and his life —one of persistence, work ethic, vision, and never giving up — that make him an inspiring Black hero of music. Diddy was fired from Uptown records, and founded Bad Boy. He almost quit the business entirely when his close friend and the biggest star of Bad Boy, BIG, was shot and killed in 1997, but after hearing The Police’s “Every Breath You Take” on the radio, decided to give it another shot with the emotional tribute to BIG “I’ll Be Missing You”, which was the first rap song to debut at number one on Billboard. He put together the Hitmen, whose production helped his remaining artists dominate the charts in the 90s, with lasting hits that you still hear all the time, like “Feel So Good” by Mase. Bad Boy’s success in turn inspired icons like Jay-Z to found his own Rockefeller label. Now, nearly 20 years after entering the music industry, Diddy has officially hit “mogul” status. He has built multiple businesses, founded two schools — one in Harlem and one in the Bronx — and he’s also a dad, and a very visible, and proud Black father to his children.

That’s why I chose the songs I did. In Netflix’s amazing docuseries HipHop Evolution (definitely watch if you haven’t), James Cruz describes Combs Diddy’s mark on music as not only creating songs that made you dance, and made you feel good, but for leaving people “with words: ‘can’t stop, won’t stop’, ‘never give up’; that inspiration… is the most impactful thing about Sean Combs.” I have to agree, and “Coming Home”, to me, is the epidomy of a comeback song.

“I thought I told y’all that we won’t stop / ‘till we back cruising through Harlem, these ol’ blocks / is what made me, saved me / drove me crazy
Drove me away / then embraced me / Forgave me / Let the rain / wash away all the pain of yesterday / I’m coming home / Tell the world I’m coming home”.

Hard not to feel inspired.

6. “Reach Out (I’ll Be There)” — The Four Tops

Motown produced so many incredible acts, but for me, The Four Tops are quintessential Motown, singing some of the catchiest songs, classy yet soulful in their matching suits. You can put “I Can’t Help Myself (Sugar Pie, Honey Bunch)” on at just about any wedding, for just about any generation, and people will connect to it and start to dance. Truly a timeless love song. But “Reach Out (I’ll Be There)” is my all-time favorite.

The incredible introduction is incredible — the creative horse galloping is such a nice touch — and somehow manages to evoke the mystery of Westworld, the excitement of The Mask of Zorro, and the romance of Casablanca. Such a simple melody, but also such a powerful one. The verse picks up steam as with Levi Stubbs delivering timeless lyrics about being there through thick and thin for the person you love, with the unwavering strength of “You’ll Never Walk Alone”, but with an urgency that feels like it could cut through even the most difficult of crises. And the chorus combines that urgency with the romance and mystery of the introductory melody.

Ironically, the group felt the song too odd to release, and begged Barry Gordy not to. Thankfully, Gordy felt differently, and so did the rest of the world, with the song going to number one in multiple countries, and becoming what many would consider to be the Four Tops’ signature song.

If you feel that you can’t go on / Because all of your hope is gone
And your life is filled with much confusion / Until happiness is just an illusion / And your world around is crumblin’ down / Darling, reach out, I’ll be there.

What’s not to love? Also, for fun, check out this video of The Four Tops vs. The Temptations.

So entertaining. Two super groups.

8. “Blue Sky” & “The People” — Common

Jay-Z once rapped “Can’t leave rap alone, the game needs me”. I agree with that statement, and I’d say the same about Common — not only for the music, but for the thoughtfulness, the vulnerability, and the heart that he has contributed to hiphop over the years. He is a voice, and a presence that is needed.

For me, “The People” most represents the embodiment of that ethos. So thoughtful, so intelligent. The beat is amazing, produced by his fellow Chi-Town native, the once great Kanye West (before he became determined into embodying the polar opposite of Common).

And then “Blue Sky” is just one of my favouite hiphop songs of all time. The beat alone is incredible — a sampling of the eclectic and beautiful “Mr. Blue Sky” by Electric Light Orchestra — into one of the hardest hitting beats every made.

Listen to that, then listen to how Common did it. The beautiful melodies and soulful patterns reshaped into one of the most hard-hitting, inspiring, uplifting, powerful beats ever made. And then Common singing: “It all started with a dream”… “Open my eyes, yes sir this is what I’m made for”… “I’m gone now, imagine what I’m gonna be”. Amazing. What a triumph.

8. “Run This Town”, “California King Bed”, & “We Found Love” — Rihanna

A legend of legends, Rihanna is in a class of her own. Choosing three songs was next to impossible, because Rihanna owns so many lanes.

She can be as street as anyone, and her voice and melodies make her hard-hitting records 10x as anthemic as anyone else’s. “Rude Boy”, “S&M”, “B*tch Better Have My Money”, “All Of The Lights”, “Take Care” all come to mind. I don’t even know where you would put “Diamonds”, but that was the other song that was incredibly hard to leave off this list. But “Run This Town” has to be her most epic, most street hook of all time.

She can do monster dance hits. “Pon de Replay”, “Only Girl In The World”, “Umbrella”, “Don’t Stop The Music”, “Shut Up & Drive”, “SOS”, “This Is What You Came For”, “What’s My Name”, “Disturbia”. That list would truly take the rest of this blog. But I put “We Found Love” because it has to be the most iconic. How many millions of people could sing along to not only the chorus, but the verse, and the pre chorus as well?

And Rihanna can actually blow people away with her ballads — the songs that demonstrate the range of her voice. The haunting and haunting yet powerful and defiant chorus of “Love The Way You Lie”, ; the playful attitude of “FourFiveSeconds” that gave Paul McCartney his first Top Five hit in 31 years. The retro “Love On The Brain” is one of my all time favorites, especially the pre chorus, which borrows melodies from Lyndyrd Skynyrd’s “Free Bird”. But “California King Bed”, and specifically the final pre chorus and chorus when Rihanna really lets it fly around (3:35 on the video) is amazing. Hands down one of the most epic ballads of all time. Also just great writing.

“So confused, I wanna ask you if you still love me, but I don’t wanna seem so weak”.

Such a raw and vulnerable line. I remember back when this song came out thinking “Wow —I can relate to feeling like that on the inside, but singing that line when I was in that place? You don’t even want to say it out loud to yourself because that’s how fragile things have gotten”. But she captured that zone perfectly.

And last but not least — Rihanna’s got some of the best remixes — most of them by The White Panda. A few of my favorites: “Diamonds” vs. Game of Thrones, “We Found 212”, and then this jam, which was always on my gym playlist; 0:37 is where it really gets good.

9. “The Morning”, “Starboy”, & “Moth To A Flame” — The Weeknd

Scarborough in the house!!! But seriously, props to Abel for reinventing himself over and over again, and for having one of the best eyes for fashion, concept, vibe, and mystery, probably of any artist in the last 10 years. The Weeknd’s arguably got better party songs — “Party Monster”, “The Hills” — and I don’t really have any of his dance songs on here, but to me, these three songs represent what I love most about him — continuing to evolve his sound over the years. “The Morning” is his all time best in my opinion. I still remember hearing it for the first time — the guitar and intro sounding like something out of a dream, and then his voice, singing about his laser focus on making it: you knew this guy was going to be huge.

Sky’s gettin’ cold, we’re flyin’ from the north /
Rockin’ with our city like a sold out show /

Order plane tickets, Cali is the mission /
Visit every month like I’m split life livin’ /

It’s tough to put “Starboy” ahead of “I Feel It Coming” but that’s the ego that’s The Weeknd for me, even though the latter might feel more lasting of a legacy. “Starboy” is all of the attitude and confidence gained since House of Balloons bottled up into an incredible song with Daft Punk (of course). That entire concept album with the Black Panther, as he snarls “I’m a m*therf*ckin’ Starboy”.

And then “Moth To A Flame” is Abel in his futuristic phase, orbiting the earth with Swedish House Mafia, another legendary EDM supergroup. Darkness, synth, future, melody, mystery. The Weeknd does that vibe like no one else, really. Someone who is not only a legend, but constantly pushing his own boundaries and exploring what’s next.

10. “Juicy” & “Old Thing Back” — Notorious B.I.G.

“Damn right I like the life I live / because I went from negative to positive”

The one and only. A poet gone far, far too soon. It’s wild that him, Busta Rhymes, DMX, and Jay-Z were all in high school together. What a class. It’s also sad how close he and Tupac were, before everything went to sh*t. Rest In Peace to two legends.

Not much else needs to be said here, honestly. “Old Thing Back” is ego, swagger, and confidence in their purest forms, and Matoma’s tropical remix specifically gives it a vibe that you can drive to, dance to, chill to, you name it. His most famous remix by a mile. It’s not just ego, either.

“All I do is separate the game from the truth” is a line that feels haunting when you know what’s to come. BIG and Tupac — as were most rappers in that era were wrapping about the gangster lifestyle. The “game”, inspired by the “truth” — real life experiences but embellished and/or moved from third person narration to autobiographical in order to stir controversy and sell millions of records. But the murders of BIG and Tupac felt like Bad Boy and Death Row, and rap as a whole, were no longer being able to separate enough game from the truth, and were in fact actively making everybody’s truth worse.

In my mind, “Juicy” could be said to be the most influential hiphop song of all time. Definitely the most iconic song about “making it”. The intro is great — dedicating an iconic song to teachers who told him he’d never be anything — but it’s that first line “It was all a dream, I used to read Word Up! magazine” — that cements it in history. So many rap songs have followed suit. This song has become the dream. From nothing to something. From scraping by to making it. From people laughing at your dreams to telling friends they used to know you. Every line in this song has been emulated by 50 Cent, Ye, Drake, you name it.

“Girls used to diss me / Now they write letters ’cause they miss me”

“Remember Rappin’ Duke? Duh-ha, duh-ha / You never thought that hip-hop would take it this far”

“Super Nintendo, Sega Genesis / When I was dead broke, man, I couldn’t picture this”

“Livin’ life without fear / Puttin’ five karats in my baby girl’s ear”

“Lunches, brunches, interviews by the pool
Considered a fool ’cause I dropped out of high school
Stereotypes of a black male misunderstood
And it’s still all good”

“We used to fuss when the landlord dissed us
No heat / wonder why Christmas missed us
Birthdays / was the worst days
Now we sip Champagne when we thirsty
You’re damn right, I like the life I live
’Cause I went from negative to positive”

So many iconic lines, that will live on forever. In music, some themes are universal, and will never go out of style. Falling in love is one. Heartbreak another. Politics. Grief. Celebration. Feeling lost. Being yourself. But the theme of “making it” cuts deep, in a more urgent, and fiery way than romance, or celebration. Songs about the come up light a fire in not only other aspiring musicians, but in people across all disciplines, all industries, if they can see their own dreams and hopes reflected in a song about bettering one’s life and proving others wrong. “It was all a dream” but I made it happen — and you could too. That’s the hope and the beauty of BIG, and songs like this.