Mac Miller & Ian Wolfson

When it comes to rappers and their music videos, there’s a lot to be scoffed at. It’s pretty easy to get on the Internet and find some laughable hip-hop videos, and it’s even easier to confuse artists with another based on the lack of content in these videos. But it’s not just content they’re lacking: it’s a strong, driving force on the other side of the camera lens that pushes them to new artistic limits. Luckily for Mac Miller, he’s had that force on his side for quite a long time now.

Ian Wolfson, also known as Rex Arrow, started Rex Arrow Films after graduating from Columbia University. He’s known Miller since the good ol’ days of Easy Mac and has been directing videos for him for nearly as long. The two both attended Taylor Allderdice High School, albeit at different times, leaving Wolfson nine-years older than Miller. Despite the age difference, the two struck a chord and since then they have worked together almost exclusively, creating over 25 videos that have garnered over 600 million views. Most all of Miller’s popular videos have come from Wolfson: “Kool Aide & Frozen Pizza“, “Senior Skip Day“, “Knock Knock“, “Donald Trump“, “Frick Park Market“, “Smile Back“, “Loud“, “S.D.S.“, “Watching Movies“, “Diablo“, and “Brand Name“, the last of which appears on his first major label album, GOOD AM.

Wolfson & Mac on the set of “Frick Park Market”

Considering the major artistic maturation and progression Miller has shown since his early mixtape days, it’s truly impressive that he and Wolfson still have a strong connection that works so well. Early videos like “Cruisin‘” and “Live Free” carry with them a clear DIY aesthetic that’s mirrored by the music: the grainy, day-in-the-life style matching Miller’s old-school beats and youthful rhymes. As his music became more colorful and “fratty” on K.I.D.S. and Best Day Ever, Wolfson figured exactly how to reflect this. It’s here where we get to some of the videos that helped in launching Miller’s online presence and overall career. “Senior Skip Day” and “Kool Aide & Frozen Pizza” featured a brighter vibe, a clearer vision, and a much more confident Miller who was finally starting to take over his city. And then “Donald Trump” happened.

It’s even funnier now to look back at this track considering “President” Trump’s new role in the national theater, but once there was a time when young rappers just wanted to emulate his money-makin’ lifestyle, a concept that Miller encapsulated perfectly in “Donald Trump”. The video, which features Miller rocking his own merchandise, has him dreaming about bumping parties in his new rap lifestyle as he continues to grow in popularity. It was a major hit, gaining tens of millions of views and blasting Miller into everyone’s playlist, but at the same time temporarily cementing him as the king of the “frat rap” boom of the early twenty-tens. To this day it still stands out as the duo’s most viewed video, racking up 124 million since it’s initial release.

“Donald Trump”

At this point in their career, it would seem that most artists would make the jump to working with more well-known directors. However, Miller’s continued independent approach to his music fueled his relationship with Wolfson and they continued on to make videos for his debut album, Blue Slide Park. Though generally panned by critics, the music from BSP had a young, happy Mac rhyming about his newfound fame and (relatively small) fortune, and Wolfson captured that cheerful spirit in some of their sillier videos. “Party on 5th Ave” had the rapper and his buddies dressed up as old men, complete with canes and graybeards. In “Frick Park Market”, we saw Mac working at his favorite local deli and rocking a goofy, white afro. It’s in this video that we also get a look at the Mac to come. While taking out the trash, he enters through a random blue door into a world of neon colors and dancing girls, the exact type of psychedelic aesthetic that would appear over his next two releases and their accompanying music videos.

After a highly-criticized first album, Miller struck back with 2012’s Macadelic, presenting us with a side of him we had never seen before. Working with a slew of new producers and collaborators, Miller’s music took on a vibe for the psychedelics. Gone were the lyrics about smoking with his homies and enjoying the spoils of fame. Here we were presented with an introspective Mac who pondered on topics like his relationship with his parents, religion, more serious drug usage, and the downfalls of fame. Macadelic marks the beginning of a new phase in Miller’s career, one that rid him of the frat rap label, and Wolfson had to be aware of this change in sound and style. Though they only worked together on two of the four videos coming from the tape, it’s clear that the change was within Wolfson’s vision as well. “Loud” was arguably their most popular video since “Donald Trump” and it seems to pick up right in the same room that “Frick Park Market” ended in. This time around, though, it seems to be much more drug-fueled, specifically lean. Miller has spoken openly about his addiction to the purple drink during this phase, and “Loud” proves he’s honest in his retelling. Flashing a toothy smile and holding a large styrofoam cup that reads “Don’t Do Drugs”, Mac starts off with the line “I got codeine in my cup/You can bet your ass I’m sippin’”. From there we see him stunting in neon glasses and jackets as neon-painted girls dance amid the black backdrop and flashing purple lights, clearly an association with lean. The second video, “Clarity“, is an example of the other half of Macadelic; it’s much more artistic in approach and features a calmer Mac rapping about love, suicide, and drugs in a more somber tone, clearly reflected by the white background as oppose to the darkness in “Loud”. Macadelic gave us a look at new Mac, and his sophomore album would continue on this road to self-reflection.


Watching Movies With the Sound Off featured much of the same subject matter as Miller’s last project, but applied to a much wider audience. Handling production mostly on his own, with the help of Pharrell, Flying Lotus, The Alchemist, and more, Miller continued to distance himself from his old persona with mesmerizing, crafty production that would please Day One fans as well as those who hopped on after Macadelic. As Miller took more creative control of his sound, so too did Wolfson in his craft. Since Macadelic, his visuals were much more concrete in style and more solid in concept, and with WMWTSO, the two decided on a narrative to play out with the album’s videos. In a 2014 interview with Mass Appeal, Wolfson spoke on the concept, saying, “each of the singles was going to be a different genre play. So if “S.D.S.” was the superhero comedy, then “Watching Movies” is like the horror film”. This concept is blatant, as both videos unquestionably match up to their respective genres. The three other videos from the album, however, are highly introspective. “Avian” follows a cult-like dealing and an old guru rapping along to Miller’s surreal lyrics. “The Star Room” and “I Am Who Am (Killin’ Time)” follow suit, with the latter introducing us to Miller’s alter-ego, Delusional Thomas. Both videos use a mirrored box full of colored light bulbs, seemingly representing his newfound self. But sometimes such overt self-reflection and drug usage warp the mind, something Wolfson captured perfectly in “The Star Room”. In a hotel room that could only be compared to Raoul Duke’s in Fear & Loathing in Las Vegas, we witness Mac continue to question his life and his role in hip-hop under the influence of some ungodly concoction of pharmaceuticals. The wavy camera usage and dark imagery (a cartoonish depiction of Satan is rendered on the wall that reads “I’m Not Real” in blood-red writing) capture the depressing hysteria that Miller has found himself in, once again proving that his own artistic progression can be thoroughly tracked through Wolfson’s videos.

Following the critical praise awarded to WMWTSO, it could be assumed that Miller entered into a lighter and more positive phase of his career. But that’s the exact opposite of what came to pass. Instead, Miller entered into a period of reclusiveness and serious drug use that left him spiraling away from any sense of sanity. It’s here that we got what many consider his magnum opus, Faces. The mixtape, released on Mother’s Day, 2014, still held on to some of that psychedelic vibe, but this time around he infused it with a jazzier sound. Lyrically, the mixtape saw Miller at his most depressed and drug-addicted, with references to using a full cornucopias-worth of drugs. The introspection and self-reflection remains, but it’s here that we witness Miller realizing how fucked up he is and not actually caring. It’s here that we witness his steps toward self-destruction, something he’s acutely aware of, but at the same time doesn’t step out of. It’s here that we witness the final nail slamming into the coffin that was his old self. It’s dark, it’s moody, it’s sometimes depressing. It also spawned only one music video, “Diablo“, of course directed by Wolfson. This one is interesting. While the song reminds us that “Everybody got dead homies”, the video is surprisingly light-hearted at first. Mac, wearing a red jacket and a captain’s hat, pulls up in an Old Jewish van to deliver cupcakes to a crowd of friends and fans in the LA sunshine. But as Miller continues to rhyme, the crowd stands in a respectful silence, possibly representing all those who are continuing to watch him spiral downward in helpless fashion. It’s probably better off that Faces only produced one video, considering most fans, including myself, wouldn’t want to see Mac in such bad shape cemented forever in a video.

“I Am Who Am”

Bouncing back from an obvious low point, Miller greets his new and improved life with GOOD AM, 2015’s album that saw him coming out of his dark spell and moving on to brighter concepts and ideas. No more are there lyrics filled with depression and drugs. Instead we get an honest optimism that shines out on his road to recovery as he leaves the demons behind him. The album also stands as his first on a major label after signing a $10 million dollar deal with Warner Brothers. However that didn’t stop him from working with Wolfson, who used the video for “Brand Name” as a reflection of the new Mac Miller. The video is a play on The Truman Show; Mac finds himself in a reality show that everyone but him is in on. After realizing his every move has been recorded for all to see, he attempts to break out of the system he’s been placed in by removing the plug from the cameras. This represents Mac breaking free from his drug use and past lifestyle. The audience, i.e. us, have been watching him for years, through all of his trials and tribulations, and we’ve come to expect certain things from him. However, he’s not going to remain that way, as he breaks out of his own box into a new one. If Faces put the nail in the coffin that was the frat rap Mac, then GOOD AM is the death of the Mac we came to know on Faces, and Wolfson’s version of The Truman Show makes for a perfect video representation to that effect.

That brings us to their most recent collaboration, “Dang!” The song appeared on Miller’s fourth album, The Divine Feminine, released this past September. If there’s one thing that’s clear from this video, it’s that Mac Miller has gone completely pop, but in the most fashionable way possible. The album wraps itself around a strong love concept, and “Dang!” kicked that off with a poppy half break-up/half make-up song that begs the question, “How many mistakes do it take till you leave?” Full of exceedingly bright colors, dancing extras, and a jive-walkin Miller, there’s no sign of the old, dark and depressed artist we were used to. We get a visual that’s just as groovy and straight-forward pop as anything Bruno Mars has ever put out, and it works oh so well! Wolfson has captured the newfound optimism and redemption in a way that only these two could, considering all they’ve accomplished together over the years. It may not just be a girl he’s dedicating this love album to, but maybe his new life as a whole.


Looking back on Miller’s career, it’s an understatement to say that he wouldn’t be where he is today without the strong partnership he’s forged with Wolfson and Rex Arrow Films. Such a director/musician partnership is nearly unheard of in today’s music, as the industry continues on its road to “business as usual”. It’s refreshing to know that two artists have stuck together from day one and continued to progress in each other’s shadows. As they continue to move forward in their respective fields, it’ll be amazing to watch what they’re able to accomplish together.