Damian Lillard recently released his rap album “The Letter O” under the moniker of Dame D.O.L.L.A. It’s worth noting that any album with Juvenile on it, regardless of genre, is automatically good. Don’t believe it? Listen to the song “Legacy.” The pained humming of Juvenile can only be matched by Kid Cudi or a chorus of God’s most beloved angels.
The cliche is that rappers want to be basketball players and basketball players want to be rappers. Lillard is the next up in a lineage that ranges from Shaquille O’Neal to Troy Hudson. And there’s plenty rappers — Master P, J. Cole, Stalley for example — who had the talent or dreamed of playing in the NBA. Like Lillard does in “Wasatch Front,” Cam’Ron once chronicled his own basketball career in his song titled “Sports, Drugs, Entertainment:”
“I can hoop, yo
All-American in my age group, yo
Grades bad, settled for a JuCo”
It’s not just that the two cultures interject, but by virtue of being dominated by the same population — American black males — they are inseparable. And often for the impoverished of that group, sports and music are two of the most attractive, and sometimes only options out. Jay Z captured this limitation perfectly on “Some How, Some Way:”
“Whether we dribble out this motherf—
Rap metaphors and riddle out this motherf—
Work second, hospital out this motherf—
Somehow we gotta get up out this motherf—
The most infamous of the basketball-rapper group was Allen “Jewelz” Iverson, whose single “40 Bars” was criticized heavily by advocacy groups and then-NBA commissioner David Stern:
"The lyrics that have been attributed to Allen Iverson's soon-to-be-released rap CD are coarse, offensive, and anti-social. Whatever constitutional rights of free speech an individual may have, there is no constitutional right to participate in the NBA and I have the power ... to disqualify players who engage in offensive conduct — including inappropriate speech."
Stern would later institute the insidious NBA dress code, a direct attack on Iverson’s personality and part of the effort to move the NBA away from hip-hop culture. Before his Hall of Fame enshrinement, Iverson came to his own defense once again. He said that he dressed the way that he did because that was the culture that he grew up in. It was an extension of his self and his greater community.
Now removed from his playing days under Stern’s watch, Iverson’s once-divisive self is now widely celebrated. In that same interview, Iverson said the experience had been bittersweet. On one hand, he was demonized unfairly. On the other, it was his struggle that empowered the future generation to unapologetically be themselves, whether through their general attitude, clothes, or creative pursuits.
A few months later, a commercial for Lillard’s album aired on one of the league’s broadcast partners during Portland’s loss against the Clippers.
The weirdness of that event is in how normal it was. Where NBA rappers would have been admonished years ago for not sticking to sports, Lillard’s foray was celebrated. Where the general demonization of rap would have caused uneasiness about the project, Lillard’s endeavor was supported by the league, his fellow players, and the fans.
A big reason is that social media has helped Lillard to not only showcase his own skills, but to use rap as a connecting link with the rest of the world. His famous #4BarFridays that he started in 2013 challenged fans and his colleagues to display their skills at the end of each week. Draymond Green, Paul George, and even LeBron James have been participants.
Lillard, of course, always had the best bars. This, along with his appearance on Sway In The Morning, legitimized him so well that by the time he was —in my opinion— winning Chance the Rapper’s #SoGoneChallenge, his ability and wholesome approach were highly regarded. He was good, fun, and clean.
In terms of technical skill, Lillard is the best among the basketball player-turned-rappers group. Shaq may be the king of sales, but Lillard makes the rest of them seem elementary. Without even the player-turned-rapper qualifier, he’s just good at rapping.
The usual defect for young rappers (or young creatives in general) is that they overcompensate. They try too hard in an effort to prove that they belong. Kobe, for example, tried to imitate Canibus so much on his single “K.O.B.E” that his rapid-fire, faux-intellectual style became laughable.
Lillard doesn’t do that. He has confidence in his flow. It’s become so well-developed and personal that he comes off more as a veteran of the game rather than a rookie. His niche seems to be storytelling, and he mirrors Kendrick Lamar’s first album in depicting scenes without making himself an active participant.
There are some exceptions. On the track “Hero,” he talks about personally being held up at gunpoint, his failed classes, and fractured relationships. But even there, when the subjects are that intimate, he speaks on them abstractly. The track is in first person, but he tells instead of showing.
This afflicts his other songs, as well. In “Wasatch Front,” Lillard raps about the struggles of his early basketball career and his dream of playing for Jerry Sloan and the Jazz. But it’s very surface-level and thus doesn’t engage the listener emotionally as it should. He could have instead used one instance of being cut from a team and working to rise above that failure to capture the essence of the grander conflict. It’s a good song, but it’s passive. But to be fair, that’s a criticism that could be leveled at most rap songs.
The album, like most from the genre of rap, has a rags to riches theme. Mixed in with Lillard’s penchant to rap like a motivational speaker, the whole thing feels like an infomercial about the American Dream. That ideal is perfect for rap and sports. Poor kid who makes it out of a bad neighborhood, away from drugs, guns, violence, and general poverty, to become a star in the NBA is an easy summary of every profile or motivational sports ad made. If you replace “NBA” with “the music industry,” it becomes the summary of most rap.
The problem, though, is that rap usually has a side of the cold, despairing reality alongside that dream. That’s not present in Lillard’s album. After those first few lines in “Some How Some Way,” Jay Z says, “I don’t always want to be this drug-dealing motherf—, damn.” That cynicism, the realization that the rapper could very well been part of the rule rather than the exception, is pivotal to the music.
This contrast is starkest on the best song of Lillard’s album, “Loyal to the Soil” feat. Lil Wayne. Lillard begins by rapping about the struggles of the environment that reared him, the difficulty of being “crabs in a barrel,” and the importance of familial closeness during times of adversity.
“I grew up ‘round love but we had a slower start
Hooping on the tree and fighting at the park
Luckily we had guidance, we was more blessed than others
We was the deepest family, nobody had more cousins”
On the next hook, Lillard, through some lyrics that could have appeared in a D.A.R.E commercial, explained why he persevered.
“I won't let that money define me
I let my struggles refine me
I know my angels behind me
Young, rich, and in the sticks tryna find peace
I ain't get high and I ain't sell dope
People ask ‘why?’ I did it for my folks”
He then urges the listener to have hope, take the plan seriously or “watch it go in smoke.”
And then Lil Wayne comes in and pours cold water on his idealism. Wayne’s first line echoes the realistic hope sentiment “Uh, chin to the clouds, all 10 on solid ground,” but he then talks about doing drugs. By the fourth line, he’s mentioned his dead father. And at the end of his verse, he labels New Orleans, his hometown, as a hell.
Where Lillard tries to be as uplifting as possible, almost purposely avoiding the hard subjects, Wayne brings in the anguish of the true world — a reminder that violence, death, and destruction can’t be glossed over.
This split goes a long way in explaining the difference between the critical reception of Lillard’s album now versus Iverson’s song 15 years ago. Lillard takes a motivational, socially-conscious and clean, if not scrubbed approach, whereas Iverson’s was much more violent. Iverson invoked guns and death in almost every line of that song, and while it may be the sensationalized reality of his childhood environment, it wasn’t suitable for a family-friendly NBA.
The times have changed, and so has rap. The gangster rap era is over, and the music now is much more fun and uplifting. Thus, the league is more receptive of one of its stars being a rapper. But even with that, even in this new environment, Lillard still has an obligation as a role model to not delve too deeply into the subjects that Lil Wayne otherwise can. He doesn’t have the full freedom of an artist.
“The Letter O” is a good album and Lillard is a very skilled rapper. But at the end of it, you can’t help but feel that he wants to address certain subjects, but can’t for whatever reason. His old song “Bigger Than Us” is where he has that freedom. Even though it still plays into his non-conflictive motivational speaker motif, that track is much more representative of his full talent.