20 Questions

Questions to Ask a Rapper

Engaging questions to connect with rappers, exploring their creative process, musical influences, and the art of hip-hop while respecting their craft and cultural contributions.

1

What got you started in hip-hop, and what keeps you passionate about the culture?

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Why this works

Reveals their hip-hop origin story and current motivations, showing what aspects of the culture they find most meaningful and inspiring.

2

What's your creative process like when you're writing a new song?

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Why this works

Explores their artistic approach and methodology, revealing how they channel inspiration into finished tracks and what drives their creativity.

3

Who are your biggest musical influences, and how have they shaped your style?

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Why this works

Shows their musical heritage and influences, revealing the artists and sounds that have shaped their approach to hip-hop and music.

4

What's the most challenging aspect of being a rapper, and how do you handle it?

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Why this works

Reveals their struggles and coping strategies, showing how they navigate the difficulties of the music industry and artistic expression.

5

What's your favorite song you've written, and what makes it special to you?

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Why this works

Encourages sharing of their proudest work and personal connections to their music, revealing what they value most in their artistry.

6

How do you approach storytelling in your lyrics, and what stories do you want to tell?

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Why this works

Explores their narrative approach and artistic vision, showing how they use music to communicate messages and share experiences.

7

What's the most important message you want to convey through your music?

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Why this works

Reveals their artistic purpose and values, showing what they hope to communicate and achieve through their music.

8

How do you handle criticism and feedback about your music?

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Why this works

Shows their approach to growth and learning, revealing how they process feedback and use it to improve their craft.

9

What's your favorite part of performing live, and what makes a great show?

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Why this works

Explores their connection to live performance and audience interaction, showing what they value most in the concert experience.

10

How do you stay authentic to yourself while appealing to your audience?

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Why this works

Tests their balance between artistic integrity and commercial success, revealing how they navigate authenticity in their music.

11

What's the most meaningful feedback you've ever received about your music?

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Why this works

Shows what kind of input they value and how they process praise or criticism, revealing their growth mindset and values.

12

How do you approach collaboration with other artists?

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Why this works

Reveals their approach to working with others and their understanding of the collaborative nature of music creation.

13

What's the most challenging verse or song you've ever written, and what made it difficult?

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Why this works

Shows their experience with complex creative challenges and their perseverance through difficult artistic projects.

14

How do you handle the business side of being a rapper?

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Why this works

Reveals their understanding of the music industry and their approach to managing the commercial aspects of their career.

15

What's your favorite hip-hop tradition or element, and why is it important to you?

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Why this works

Shows their respect for hip-hop culture and traditions, revealing what aspects of the culture they value most.

16

How do you approach freestyling versus written lyrics?

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Why this works

Explores their different creative approaches and skills, showing how they balance improvisation with planned composition.

17

What's the most important lesson hip-hop has taught you about life?

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Why this works

Reveals how they connect hip-hop to broader life lessons, showing their perspective on the culture's deeper meaning.

18

How do you handle the pressure of representing hip-hop culture?

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Why this works

Tests their understanding of their role in the culture and their approach to the responsibility of being a hip-hop artist.

19

What's something you wish more people understood about hip-hop?

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Why this works

Gives them a voice to share their knowledge and helps others understand the complexities and importance of hip-hop culture.

20

How do you see your music evolving in the future, and what new directions interest you?

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Why this works

Shows their vision for their artistic development and their openness to growth and change in their music.

Best Practices for Conversations with Rappers

Expert tips and techniques for getting the most out of these questions.

Best Practices

Respect the Culture

Show respect for hip-hop culture and its history, and avoid making assumptions about the genre or its artists.

Ask About Their Art

Focus on their creative process, influences, and artistic vision rather than just asking about fame or success.

Listen to Their Stories

Rappers often have powerful stories to share. Listen actively and show genuine interest in their experiences and perspectives.

Question Sequences

The Creative Journey

1
What got you started in hip-hop?
2
What's your creative process like?
3
Who are your biggest influences?
4
What's your favorite song you've written?

The Artistic Vision

1
What's the most important message you want to convey?
2
How do you approach storytelling in your lyrics?
3
What's your favorite hip-hop tradition?
4
How do you handle the business side?

Common Pitfalls

Don't Make Stereotypical Assumptions

Avoid making assumptions about their background, lifestyle, or values based on stereotypes about rappers or hip-hop culture.

Don't Focus Only on Fame

Avoid reducing the conversation to just fame, money, or success. Focus on their artistry and creative process.

Don't Interrupt Their Flow

Allow rappers to share their experiences fully before asking follow-up questions or sharing your own stories.

Conversation Templates

The Artistic Introduction

1
Step 1: Start with: "I'm curious about your journey in hip-hop. What got you started in the culture?"
2
Step 2: Follow with: "What's your creative process like when you're writing?"
3
Step 3: Deepen with: "What's the most important message you want to convey through your music?"

Further Reading

"The Rap Year Book" by Shea Serrano
"Hip Hop America" by Nelson George
"Can't Stop Won't Stop" by Jeff Chang

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