On Wednesday night in Salt Lake City, Portland Trail Blazers guard Damian Lillard put up 25 points in 29 minutes in a preseason win against the Utah Jazz. The next morning, Dame D.O.L.L.A. — Lillard’s hip-hop pseudonym — dropped his new music video for “Money Ball.” Later that night brought another preseason game for Lillard, this time versus the Nuggets in Denver, and the following morning Dame D.O.L.L.A. readied the deluxe-edition release of his best album to date.
This balancing act is the new normal for the All-NBA athlete hoping to conquer the Bo Jackson-esque task of ascending to the zenith of two viciously competitive arenas. “It’s been a really good stretch for me as far as basketball and my music. I think this is just the beginning,” Lillard tells Rolling Stone. “Anytime you’re doing something like this, when you have two occupations, planning is important. Everything is coming together nicely because of our plan.”
For Lillard, the start of the 2019-20 season marks the end of the most prosperous summer of his career as both a basketball player and a rapper: First, he eliminated the Oklahoma City Thunder with “The Shot” — a no-time-left, hand-in-face, 37-foot 3-pointer that singlehandedly upheaved the Thunder franchise, launched countless memes, and thrust “Dame Time” into the viralsphere — and led the Blazers to the Western Conference Finals. After Lillard re-upped his commitment to Portland with a huge extension, Dame D.O.L.L.A. released his third album, Big D.O.L.L.A., his strongest and most complete statement as a hip-hop artist yet. The album, a 10-track collection of what he calls “pure” rap songs, showcases Lillard’s nimbleness and versatility as a rapper — qualities he shares as an all-star point guard.
Big D.O.L.L.A. arrived this summer with guests like Lil Wayne (a frequent collaborator), Jeremih, and Mozzy alongside emerging artists like Marley Waters, Brookfield Duece, and more. The guest list increases on the just-released digital deluxe edition of the LP, with Lil Durk, Jadakiss, Benny the Butcher, and fellow Oakland native G-Eazy hopping on Big D.O.L.L.A. remixes.
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“When you’re getting up-and-comers and you’re getting legends, you’re getting that kind of company, that’s a huge co-sign, especially when you’re an athlete doing it,” Lillard says. “So that means a lot to me, keeping that kind of company on my music consistently.”
While no one doubts Lillard’s ability to drain 3-point shots from astonishing distances, Dame D.O.L.L.A. found himself having to reassert his talents every offseason. “In the past, I would do my albums and all my music in the summer, and when the season started, it would completely go away,” he says. “So it was hard to keep the audience and keep people’s attention and keep it fresh in their minds, where they’re treating me like an artist.”
To keep pushing forward on his music career — tracks off Big D.O.L.L.A. have recently graced tastemaking Spotify playlists and soundtracked TV shows like HBO’s Ballers — he formulated a plan so Dame D.O.L.L.A. could stay active while Lillard concentrated on basketball.
“This summer, we recorded enough music where I could be rolling it during the season. For example, if it’s a big game, I have music ready to go,” Lillard said, teasing NBA holidays like All-Star Weekend, the Christmas slate, or just a Dame Time-dominated game as a potential landing spot for new music.
“One of my friends who I grew up with at home who’s an up-and-coming artist, Tree Thomas, me and him have a mixtape called D.O.L.L.A. Tree that we have already done that I’m going to put out at some point during the season,” Lillard says. “I’m just making sure I have music to release during the season so it doesn’t go completely dead. It’s stuff like that where I’m not losing momentum and I’m not just disappearing after doing a bunch of music.”
That “bunch of music” included a pair of diss tracks aimed at retired basketball star Shaquille O’Neal, perhaps the NBA’s first bonafide(ish) rapper but someone who was instantly overmatched in his battle of words with Lillard.
O’Neal fired the first salvo after Lillard stated on the Joe Budden Podcast that he was a better rapper than Shaq. Two D.O.L.L.A. songs later — “Reign Reign Go Away” and “I Rest My Case,” the latter appearing on the Big D.O.L.L.A. deluxe edition — Lillard claimed victory. Part of what made Lillard’s lyrical evisceration of Shaq so devastating was the immediacy and fastidiousness in which he savagely countered O’Neal’s jabs; Lillard reveals he penned “Reign Reign Go Away” in 45 minutes and “I Rest My Case” in 20.
“Shaq started the war, but — for now — Dame did more than enough to finish it,” Rolling Stone said of the beef, which came just months after Lillard engaged in an NBA Draft-night battle of SoundCloud diss tracks with the Sacramento Kings’ Marvin Bagley III. “It was fun with Marvin Bagley because it was the very first time that athletes ever did something like that — a battle rap with athletes — but even then, I didn’t think I’d do it again,” Lillard says. “But then Shaq dissed me, and he’s Shaq. I gotta go back, he’s too big of a deal.”
As studied as he is in making shots and reading defenses, Lillard is equally versed in the rap game. “I’m a huge fan of URL, the Ultimate Rap League. I’ll watch Loaded Lux and Murda Mook, and Serius Jones, all those dudes, Tay Roc, K-Shine,” Lillard says before adding, “But at this point, I think my battle rap career is over.”
Lillard’s upbringing in Oakland fostered his ability to construct rhymes. “I’ve always been able to come up with words pretty easily,” he adds. “When I was a kid, my mom’s older sister used to make me do book reports and stuff like that, even if it didn’t involve school. If I misused a word, she would make me look up the definition and use it in a sentence. I grew up in that environment so I’ve always had a very broad vocabulary, and I know something about a lot of things.”
One night earlier this month encapsulated what Lillard hopes is the perfect balance of basketball and music. On October 6th, the Trail Blazers held their annual Fan Fest at the Veterans Memorial Coliseum, the team’s former arena before moving to the Moda Center a short walk away. Minutes after his Fan Fest appearance, Lillard received a phone call from his friend and fellow rapper YBN Cordae, who was about to take the stage at the Moda Center as a special guest on Logic’s Confessions of a Dangerous Mind tour.
Look who surprised the crowd tonight at @ModaCenter 👀
— Portland Trail Blazers (@trailblazers) October 7, 2019
“Cordae just hit me like, ‘Man, come over here,’ so I walked over from Fan Fest and got onstage with him. It was pretty cool,” Lillard says, adding that a small tour of live performances is “definitely the plan” next offseason.
Lillard’s new balance is also on display in the “Money Ball” video: While he was previously cognizant about separating his job from his art, the video is rife with basketball references — Lillard calls the track an ode to the game of basketball hidden within a strip-club anthem — and even features a cameo by his Blazers backcourt partner C.J. McCollum. “C.J. is a real friend of mine; he’s more than just a teammate,” Lillard says. “We spend a lot of time around each other [and] talk every day, so that was a natural environment.”
Lillard — who earlier this week was dubbed “Best Leader” in an annual NBA.com survey of the league’s 30 general managers — recognizes that expectations for him are higher now as both a rapper and a player; after being ousted in the Western Conference Finals, the Blazers’ roster, like much of the Western Conference itself, underwent substantial changes.
“When you’ve had that kind of roster turnover, it’s gonna take time to come together and jell like we want to at a championship level, but I think we got great guys,” Lillard says. “We brought in a lot of good talent, a lot of complementary players in support of what we already had. It was enough change to create some excitement instead of the same thing over and over and over. I think we’re all excited about the season.”
Before the Blazers’ season opener on October 23rd, however, Lillard is still in Dame D.O.L.L.A. mode, discussing how the new remixes came about. Lil Wayne appeared on the Big D.O.L.L.A. version of “Sorry,” but the remix boasts the addition of Jadakiss: Dame says he brought the two rappers together as a reunion of sorts for “Death Wish,” Wayne and Jadakiss’ 2009 single and one of Lillard’s favorite songs. “I think I’d make a pretty good A&R guy,” he quips.
Lillard has been vocal about his desire for Dame D.O.L.L.A. to someday win a Grammy Award. “First, I want to win a championship. I want to be MVP of the league. But to win a Grammy? That would be tight,” he says at the end of his conversation with Rolling Stone.
Soon after the interview ends, Lillard is back on Twitter, confronted by the rapper Gage who asks, “One dream wasnt enough? now u wanna come into the rap lane smh lol.”
Like staring down Paul George in a decisive Game Five with only seconds on the clock, Lillard doesn’t back down:
What’s better than one dream? … ✌🏾 https://t.co/IGvZOyzhif
— Damian Lillard (@Dame_Lillard) October 17, 2019