An Oral History of Brandon Jennings and OVO


Photo via Hamad Alhassen

Apparently oral histories of famous sports stars and their connections to Drake’s label OVO has become our shtick. Our last oral history focused on Johnny Manziel. This time the subject of our feature is Detroit Pistons PG, Brandon Jennings. 

This is where our story begins. This is where I first learned about Brandon Jennings’ fascination with Drake. After Take Care dropped, Brandon Jennings tweeted this picture of him buying ~NINE~ copies of the album. He’s since deleted the tweet, but the picture still lives on in all of its glory.

This is Brandon Jenning’s first tweet that isn’t a retweet. Clicking the link will take you to Brandon’s account where this picture shows up.

That’s the famous owl logo that Drake uses to represent his OVO label. At this point I knew we were in for a long ride.

Brandon uploaded this to his account on the same night as the previous image, but didn’t tweet it. Smoking hookah while sitting in a lawn chair outside of an apartment complex in an OVO hoodie sounds like a Drake music video idea that got scrapped from the drawing board.

On September 11, 2012, Brandon retweeted this tweet by The Weeknd disclosing information about his debut album Trilogy. Brandon loves the crew as well.

You might remember OVONiko as one of the members of the crew Johnny Manziel shouted out on Twitter. Small world, huh?

Brandon REALLY loves the crew. That was almost a “YASSS.”

What a coincidence.

Maybe he’s more of an XO fan?

There it is. This is the first mention of a Drake lyric on Brandon Jennings’ Twitter account. It’s a quote from the song, ‘November 18th‘, from Drake’s So Far Gone mixtape.

It’s a little weird that Drake calls himself Champagne Papi already, but Brandon Jennings modeling his own nickname after Drake’s nickname is even weirder.

So Far Gone seems to be a favorite of Mr. Jennings.

There’s that Golden Papi thing again.

It seems that Brandon has moved on from So Far Gone to focus on Take Care. This is a line from the ‘Cameras/Good Ones Go (Interlude)‘. This is a great song to listen to while you stalk your crush’s Facebook page and cry—according to a friend, of course. Excellent choice, Mr. Jennings.

This isn’t even OVO related, but it’s hilarious so I’ll allow it.

How many Drake songs do you think were played at this? Probably all of them.

“So if you find a Blackberry with the side scroll, sell that mothafucka to any rapper that I know.”

Brandon Jennings turned 23 and the first thing he did was hashtag OVOXO.

Without context, this tweet is really creepy, but It’s funnier when you realize he misquoted the lyric.

Another misquoted lyric.

You don’t realize how creepy The Weeknd’s lyrics are until you see them typed out. Probably a good rule of thumb to never tweet The Weeknd lyrics.

This is a good song; I’ll allow it.

This is pretty bold.

Brandon retweeted this and I’m slowly realizing this is more of An Oral History of Brandon Jennings and XO

Never mind. He retweeted this and we’re back to OVO.

I forgot about French Montana’s ‘Pop That‘, so I’m actually pretty thankful Brandon tweeted this lyric.

Let the record show that Brandon Jennings is a big fan of ‘Fear’.

This all but confirms my theory that Drake is a huge fan of palindromes.

It’s worth noting that I’m 100% sure that this is the same red OVO hoodie from earlier.

A fun game to play is, “what’s going on that would lead to Brandon Jennings retweeting THAT The Weeknd tweet?”

WAIT, was Brandon Jennings in The Dark Knight Rises?

It’s likely that Brandon Jennings could tweet this every day, probably.

Missed you, Drake lyrics.

I’m honestly surprised this isn’t a picture of Drake or The Weeknd.



Lol at “this is getting outta hand” because…yeah…

It’s worth noting that this “No New Friends” happened almost an entire year before ‘No New Friends’ dropped. OVONiko is Drake’s ghostwriter.

You learn something new every day.

Time to play “which Montreal strip club was Brandon Jennings at on October 16, 2012?” I posit Chez Parée.

Strap in!

Not Drake.

“All rap lyrics from here on out” was short lived.

And we’re back. Also, not Drake.

Not Drake.

Not a rap lyric.

Not Drake.


So here we are. I don’t know what to do with my hands. Brandon Jennings repping OVOXO in Toronto. Can’t formulate complete sentences.

He met Drake.

Odds that Brandon Jennings has an OVO and/or XO tattoo somewhere on his body?


This is the least descriptive tweet ever.

“Odds that Brandon Jennings has an OVO and/or XO tattoo somewhere on his body?” 100%.

No one relates to The Weeknd, Brandon.




That’s four tweets about one music video if you’re keeping track at home.


Five tweets about one song. ‘VALERIE’ ISN’T EVEN THAT GOOD.

I would typically call him out for qualifying his fan hood, but BJ probably has at least two never-before-heard mixtapes made exclusively for him.


110% chance Brandon Jennings has an XO tattoo.

ICYMI earlier.

These bitches better start paying me for this. Can’t get no more free Brandon!

That’s not exactly the song that gets me in the mood to shoot around in the gym, but it could explain Brandon’s poor shooting numbers.

Maybe Brandon Jennings secretly parties with The Weeknd a lot. There’s no way a human being is a fan of an artist this much without sharing multiple drug ridden nights with them.


Wait for it…

There it is.


A classic tweet from ~REAL~ OVO fans.

Screen Shot 2013-09-22 at 6.29.47 PM

Let em know, Brandon.

Brandon Jennings and ‘The Zone’ sitting in a tree…

Nothing like a good Drake lyric tweet on Christmas Eve.



Notice he didn’t mention Drake. Is there trouble in paradise?

Brandon is either in a fraternity or this is yet another nod to The Weeknd.

I can’t imagine what New Year’s Eve was like if Brandon is tweeting lyrics to ‘Wicked Games’ beforehand.


Seems there’s no trouble in paradise after all.

It’s better if you read it as Brandon misspelling “weekend” and informing us that he has an appointment this weekend.


You know how celebrities always die in threes? Brandon Jennings always tweets about new OVOXO songs in threes.


This was uploaded on Brandon’s Instagram and is the starting point of a very deep OVOXO-Instagram rabbit hole.

So, yeah.

Ah, ‘Wicked Games’. A Brandon Jennings classic.

OVO owl sweatshirt: a staple for any OVO and/or XO fan.


This is the only Drake song Brandon knows.


I’m not really sure what to say to be honest.

I’m never listening to ‘The Zone’ again.

XO inspired clothing, I cannot.

He met The Weeknd.

Is there an advanced stat that determines Milwaukee’s win-loss record after Brandon Jennings hangs out with OVONiko?


Seriously. I bet they’ve never won.


I’m just saying.

No New Friends.

Does OVOXO pay Brandon Jennings to do promo? Serious question.

They HAVE to be paying him right? There’s no way that someone likes two artists this much.

Trust me, you’re going to see this pendant appear A LOT on BJ’s Instagram.

These are my favorite Brandon Jennings tweets. Every single one of them is like a choose your own adventure story. “Which member of the OVOXO collective did Brandon Jennings meet today?”

Every month in an XO month, Brandon.

Brandon Jennings’ iPod has 10,000 songs on it and they’re all by The Weeknd and Drake.


Truly yours, your biggest fan, this is Brandon.

Owl sweatshirt? Check. XO necklace? Check.

If you haven’t cried to this song you did it wrong.

Owl crewneck? Check. XO necklace? Check. Jesus piece? Check.


I really want those sweatpants.

There’s the necklace again.


Again, OVO sweatshirt x XO necklace is Brandon Jennings’ go-to casual look.

I didn’t even know this video was a thing. But Brandon did. Brandon knows everything.

His verse on what? A clue word would help. Is this a generalization that encompasses The Weeknd’s entire discography or is this an isolated incident? We need answers.

There it is again.

It was only a matter of time before Brandon found out about PARTYNEXTDOOR. It was bound to happen. Brandon was bound to fall in love. I expect we’ll see more of PARTYNEXTDOOR on Brandon Jennings’ Twitter account in the upcoming months.

And again.

I can only assume this is a co-sign to this Drake outfit.

You can’t fault him for being dedicated to his craft.

THAT’S AN XO NECKLACE. How do these athletes get custom OVOXO jewelry? Is there a VIP Etsy that I don’t know about?

And again.

And again.

This is the best picture ever. It looks like it belongs in Kissland.

‘Come Thru’ is a bonus track on the deluxe version of Nothing Was The Same. Is it safe to assume Brandon had an exclusive copy back in May? I’d like to think so.

Again, if you haven’t cried listening to ‘Girls Love Beyonce’ you need to. Go out and buy your favorite wine; turn the song on and set it to repeat; and go look at your ex’s Facebook page and imagine what could’ve been. It’s therapeutic.

And again.

Yep, I knew we would see more PARTYNEXTDOOR lyrics.

This will likely be engraved on Brandon’s tombstone.


Brandon thoughtfully edits out “nigga” from his tweets.

Do you guys think Brandon has an app that sporadically tweets what song he’s currently listening to? I do.

I think this is an allegory that points to the direction Brandon himself will be heading while he’s playing in Detroit. Look for him to win MVP this season.

Brandon has been listening to Comeback Season for two days now. I’m going to assume that he’s been listening non-stop for 48 hours.

Subtweet to Monta Ellis perhaps?

THIS PICTURE IS E V E R Y T H I N G. He undersold it being an “OVO night” by a lot.

When isn’t it an OVO night, really?

At first I thought this was about Roscoe’s House of Chicken & Waffles, but listening to OVO before you go and consume fried chicken seems impractical. I’ve never wanted to be sad before eating chicken and waffles. Chicken and waffles is an out-of-body experience and I want to experience joy before I consume it.

So I googled “roscoe’s nightclub” and Roscoe’s was the first result. However, Roscoe’s is a gay and lesbian themed nightclub in Chicago so that didn’t make sense. What I’m getting at is that I have no idea what this tweet is about and I’m just hypothesizing

Well, that clears that up.

A lot of very important things are happening here. 1. THAT SHIRT 2. The owl necklace 3. Brandon’s glasses?


Brandon was in his feelings that night.


Brandon does.

Gonna stop you there, too, Brandon. J. Cole was out of line for saying that. I hold you to the same standard.

This tweet is so tender; so loving. I assume this is about Drake.

Brandon clearly doesn’t feel the same way about Aaliyah that Drake does.

Legendary combination.


Do you think Brandon bought a ticket to every stop? I do.

This is a good PARTYNEXTDOOR song, so I won’t hold that against him.

THERE IT IS AGAIN. This all but confirms my theory that Brandon had an advanced copy of Nothing Was The Same this summer.

It’s like he’s an automated account only set to tweet Drake lyrics.


Likely more than one copy.

I don’t even want to know what The Weeknd’s definition of “fun” is. It’s certainly not a normal person’s definition.


It only makes sense that Brandon likes PARTYNEXTDOOR because PARTYNEXTDOOR sounds like Drake and The Weeknd layered their voices on top of each other.


Bold, but expected.

Here we are. I don’t know what to do either. If you read our oral history of Johnny Manziel, you’ll know that this Drake tweet was after the SEC Media day that saw Johnny Manziel wearing an OVO lapel pin. Brandon retweeted this tweet and set the foundation of a relationship with Mr. Manziel. But we’ll talk about that later.


I’m so happy that an OVO basketball tournament is a thing.

I can’t even imagine what these nights are like.

YEP THIS HAPPENED. There’s a lot going on here so I’ll break it down. First, this is Johnny Manziel and Brandon Jennings hanging out together. Both of them are known fans of the OVOXO movement. If you take a look at the jewelry adorning Jennings’ neck you’ll see an owl pendant and and XO pendant—both Drake and The Weeknd’s symbols. The third chain is a key which I assume is what PARTYNEXTDOOR reps. On to their hands. They’re making the OVO-owl hand sign. I don’t know how this picture didn’t break the Internet. I had to restrain myself from typing this paragraph in all caps.

No, Brandon, that’s Aubrey. There can only be one.

I love this friendship already.

Brandon Jennings interpolating Drake lyrics to make them relatable to himself will never get old.

It could happen.

What’s OVO Bounce you ask? Oh, nothing, just a BASKETBALL TOURNAMENT THAT’S SPONSORED BY DRAKE. Oh, yeah, this happened.


Of course Brandon won the OVO Bounce tournament. There was no way he was letting Drake down.

If you’re keeping score at home, that’s 1 OVO owl necklace, 1 ‘The Motion’ themed t-shirt, and 1 Toronto Blue Jays hat.

He did say it would be an OVO summer.

OVONiko deserves a raise.

Wear your OVO sweatshirts everywhere.


I think that’s a dri-fit Nothing Was The Same warm-up shirt aka something I need more than life.

“Word in New York is that Dyckman and Heights girls are calling me papi.”


It’s all happening so quickly. There’s a lot going on in this picture. Notice that the entire crew is wearing Nothing Was The Same shirts. How do I buy one of those? Also, the white guy to the stage-right of Brandon is wearing a TOPSZN Regime hat which is the same OVO collective Johnny Manziel claims.


He does have an advanced copy.


I love it so much. Johnny Manziel and Brandon Jennings > Batman and Robin.

Likely the two most important dates in Brandon Jennings’ life.

You guys remember in Toy Story when the little green aliens see the claw for the first time? Brandon likely made a similar noise when he figured out his two already favorite albums were done.

These two tweets being back-to-back are hilarious. I’ll let you figure out why.

Of course.

Johnny Manziel and Brandon Jennings > Starsky and Hutch.

It’s still hilarious that Kissland is called Kissland. Like that’s the actual title.

Show so nice Brandon caught it twice.

He’s likely still listening to it today. He’s never stopped listening.

Drake, Brandon Jennings and Johnny Football > Charlie’s Angels

I was going to ask if Brandon downloaded the Nothing Was The Same leak, but, yeah, he did.


Really need one of these shirts, too.

This was tweeted two days ago. Brandon celebrated his birthday two days later. Uh-oh.

Brandon Jennings is a genius. Drake is genius. This picture promoting Nothing Was The Same is genius.

I also need THAT shirt.

How do I buy this shirt?

Ah, this is the last OVO related tweet Brandon has tweet during this installment of the Oral History of…




You’re not surprised by this are you?


As you can see, Johnny Manziel isn’t the only athlete that loves the crew. Brandon Jennings is also a fan of the OVO collective. It’s weird, I won’t front. But i’ve also spent the better portion of 10 hours lurking the timelines and Instagrams of athletes for connections to OVO, so I can’t really talk.

Alex Hancock needs a girlfriend so he doesn’t do more of these. Follow him – @hancxck

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