With 45 videos published as of October 2026, Jubileeās Surrounded series has racked up hundreds of millions of views, with many videos garnering 5 million-45 million views. The seriesā format pits one person against a group of people with opposing perspectives, creating conversations that are entertaining, educational, and engaging. The first Surrounded video was titled ā1 Conservative vs 25 Liberal College Studentsā with Charlie Kirk; the most recent video was āAI Realist vs 20 AI Optimistsā with Andrew Yang. The channel has also featured Ben Shapiro, Pete Buttigieg, Lila Rose, Doctor Mike, Candace Owens, Bryan Johnson, and Jillian Michaels.Ā While the series has explored a variety of social, political, and cultural issues, there are still plenty of matchups I would love to see.Ā
Music & Film
Popstar vs 20 Indie Artists
What separates a superstar from an independent artist? Is it talent, marketing, industry connections, or luck? This episode could explore the music industry’s relationship with fame, the pressure to appeal to mainstream audiences, and whether commercial success necessarily reflects artistic ability. It would be especially interesting to hear how independent artists define success compared with performers who have reached the top of the industry. For the popstar, Iād love to see someone BIG: Taylor Swift, Billie Eilish, or Chappell Roan. They all are outspoken artists who I could totally see doing this.Ā
Oscar-Winning Actor vs 20 Struggling Actors
Acting is an incredibly competitive profession, and success often depends on more than talent alone. An Oscar-winning actor could discuss the realities of making it in Hollywood, while struggling actors share their experiences with auditions, rejection, networking, and financial instability. The debate could examine whether hard work is enough to succeed in the entertainment industry or whether privilege, connections, and opportunity play a larger role than people would like to admit. For the Oscar-winner, Iād love to see Meryl Streep or Jennifer Lawrence. Actors are often less outspoken than musicians, so these picks may be more of a longshot.
Academia
College Professor vs 20 Students
Students and professors often have very different perspectives on what makes a successful college experience. This episode could explore attendance policies, grading, AI, participation requirements, and the growing cost of higher education. It would be interesting to see whether professors’ expectations align with students’ experiences and whether both groups agree on what education should accomplish. For this matchup, an experienced doctor pit against sophomores or juniors from a variety of backgrounds, colleges, and majors would be perfect.Ā
College Student vs 20 College Dropouts
Is college necessary to achieve success? A passionate college student could defend the value of higher education, while college dropouts explain why they chose a different path. The discussion could address student debt, career opportunities, trade schools, entrepreneurship, and the pressure to earn a degree. Rather than treating either choice as right or wrong, this episode could examine how different circumstances shape people’s educational decisions.
Public School Educator vs 20 Private School EducatorsĀ
While private schools are often associated with smaller class sizes, greater resources, and more individualized instruction, public school educators work within a different set of funding structures and requirements. This episode could explore whether private education actually provides a ābetterā education or whether its advantages reflect issues with resources and access. I’d especially want to hear the educators discuss classroom challenges, teacher autonomy, and whether every student has an equal opportunity to succeed.
Age
Kid vs Elders (and vice versa)
An episode featuring children and older adults could explore how perspectives change across generations. Participants could discuss technology, friendship, relationships, work, education, and what makes a meaningful life. The most compelling questions would be those that allow both groups to challenge each other’s assumptions while discovering what they have in common.
Literature
BookTok Influencer vs 20 Literary Scholars
What makes a book worth reading? This episode would bring together two groups that can approach literature from very different perspectives. A BookTok influencer might prioritize emotional impact, relatability, and a book’s ability to connect with a large audience, while literary scholars might emphasize historical context, formal analysis, and critical reception. The debate could explore whether social media has made literature more accessible, whether popular books receive more attention than they deserve, and who gets to decide what counts as literary merit.
Ultimately, these are the Surrounded episodes I want to see because they would bring together people whose experiences and perspectives differ in meaningful ways. The most interesting debates are not necessarily those in which one person changes everyone’s mind, but those that reveal why people think differently in the first place. Whether the subject is education, artistic success, age, or literature, I would love to see Jubilee continue creating conversations that challenge assumptions and leave viewers with something to think about.