Rapper Mocking CEOs and Earning 13.6 Billion Won... Top Choice for Google, Goldman, and Other Business Giants

WSJ Highlights Frequent Corporate Event Rapper 'Kelly James'
Impromptu Raps Mocking CEOs and Celebrities on Sensitive Topics
"Receives Attendee List and Conducts Thorough Pre-Event Research"

"Corporate CEOs willingly pay to hire a singer who makes fun of them."

The Wall Street Journal (WSJ) recently focused on Kelly James, a 40-something rapper in the United States. James is not as famous as hip-hop legends like Drake or Eminem, but he is frequently invited to global corporate events and earns hundreds of millions of won. Last year, he attended 112 events and earned $10 million (approximately 13.64 billion won). This year, he has been invited to major corporate events hosted by Delta, Home Depot, Goldman Sachs, McKinsey, Bank of America (BoA), and others.

'Golf Emperor' Tiger Woods (photo left) and rapper Kelly James (Photo by Kelly James official website)

According to information Kelly James shared on his website, Sundar Pichai, CEO of Google, said, "I wish Kelly were at every event," and Chuck Robbins, CEO of Cisco Systems, said, "All of us at Cisco never get tired of Kelly." Golf legend Tiger Woods described his performance as "the most unique live show I've ever seen," and NBA superstar Stephen Curry said, "Amazing. If you have a big event, hire him."

The reason Kelly James receives such high praise despite not being a famous rapper is due to his performance style.

He mainly targets the highest-ranking CEOs or celebrities at events, delivering rap jokes about them. CEOs and celebrities, who usually appear reserved around him, enjoy his friendly rapper attitude. Additionally, he boldly brings up sensitive topics that event organizers might find delicate. While addressing subjects that everyone tends to avoid, he manages to keep the atmosphere light and attendees laughing without offending anyone. This is the general consensus about him.

Last year, Kelly James performed at a party related to the Masters Golf event hosted by Delta Air Lines. There, he freestyled a rap about Ed Bastian, CEO of Delta Air Lines. He used the fact that Bastian usually prefers economy seats at the back of the plane instead of first or business class. He rapped, "Ed is at the back of the plane. We know that's tradition. Many other executives are different from him. But his pet goes on vacation, on a private jet." This depicted a situation where Bastian’s wife sits in first class holding their pet, separated from her husband.

Bastian reportedly laughed heartily upon hearing this. He said, "I have never laughed that hard in my life." He also praised Kelly James as "always the best player at the Masters."

In 2022, Kelly James performed an impromptu rap on the topic of "fossil fuels" at an event hosted by the Saudi Public Investment Fund (PIF) in Riyadh, Saudi Arabia. He asked the audience for keywords to rap about, and Yasir Al-Rumayyan, Governor of PIF, gave him the keyword. This was a significant keyword given the mission from Saudi Crown Prince Mohammed bin Salman to diversify the country's revenue structure, which is heavily dependent on fossil fuels. Understanding the situation, James improvised a rap on the spot, and Al-Rumayyan was so pleased that he invited him to private events as well.

Kelly James performing at the Mercedes-Benz Masters Week last April (Photo by Kelly James)

He has also gained attention by attending golf tournament events and rapping about famous figures like Woods and Curry. Egon Durban, co-CEO of private equity firm Silver Lake, said he was drawn to James because he wanted to joke with friends like before achieving social success, and he hired James for his personal fundraising event and his wife’s 50th birthday party. WSJ reported, "Many people want to tease their bosses," adding, "Kelly James has built his career by teasing people who are not used to being teased."

Kelly James’s impromptu raps come after extensive effort. He has two staff members dedicated to pre-event research who gather all information about attendees once an event is scheduled. They collect attendee lists and compile information from articles, LinkedIn profiles, and more to understand their workplaces, alma maters, golf skills, and whether they have children. Sometimes, they even sign agreements to obtain confidential information.

James explained, "I might use 7% of the information gathered at the event, or 90%. I need to be able to rap about college football or Japan’s inflation issues." He majored in business administration at the University of Southern California, following his parents’ wishes who opposed music. After graduation, he began his music career. While working in clubs, he was invited to corporate events by brands such as Oakley (eyewear), Corona (beer), Red Bull (beverages), and Vans (shoe manufacturer), which led him down this path. He told WSJ, "People who hire me are somewhat nervous before the performance, and I am nervous too. I have to make it clear that I understand the relevant information."