Chapter summaries I'd Like to Play Alone, Please Tom Segura

Chapter 5: I Had a Dream

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

Tom Segura begins by describing the surprising voicemail he received on August 17, 2014, from rapper Big Daddy Kane. He then takes the reader back to his childhood in suburban America, where he became infatuated with hip-hop. He recalls his neighbor Dan Cote introducing him to music, and his first love: the Fat Boys. He went to the library to learn slang and wrote embarrassing rap rhymes, performing them for family. He wore a Public Enemy shirt to school, confusing his math teacher Mr. Knurr. Tom was heavily influenced by Black athletes like Deion Sanders and Black comedians like Chris Rock. After college, he moved to Los Angeles, took improv classes, and eventually tried stand-up, spending two years doing a weak Chris Rock impression. Years later, he saw Big Daddy Kane on Sunset Boulevard and impulsively shouted at him, then hid. He began telling that story onstage; it became part of his special Completely Normal. After seeing the special, Big Daddy Kane called and left a voicemail. They met at Russell Peters's house and even created a joint T-shirt. Tom concludes that putting your passions out into the universe can bring them back to you.

Key Events

  • Tom discovers a voicemail from Big Daddy Kane on August 17, 2014.
  • Flashback to age eight: neighbor Dan Cote plays hip-hop; Tom becomes obsessed with the Fat Boys.
  • Tom uses a library book to learn hip-hop slang and writes his own rap lyrics.
  • He wears a Public Enemy Fear of a Black Planet shirt to school; his math teacher is baffled.
  • Tom cites Deion Sanders and Chris Rock as major influences in sports and comedy.
  • After improv classes, he tries stand-up and unconsciously imitates Chris Rock for two years.
  • He spots Big Daddy Kane on Sunset Boulevard, shouts a greeting, then hides.
  • The story becomes a bit in his one-hour special Completely Normal.
  • Big Daddy Kane sees the special, calls Tom, and they meet at Russell Peters's house.
  • They collaborate on a T-shirt featuring both their images.

Character Development

Tom Segura evolves from a suburban kid trying to mimic Black culture into a stand-up comedian who confidently owns his influences. His early attempts to be "urban" are cringeworthy but part of his journey. The voicemail from Big Daddy Kane validates his persistence and love of hip-hop. Big Daddy Kane is portrayed as generous and encouraging, reaching out to a fan.

Themes, Symbols, or Motifs

  • Cultural Appreciation vs. Appropriation: Tom openly discusses his lifelong admiration of Black culture and acknowledges the complexities of appropriation, referencing Q-Tip and Jesse Williams.
  • Dreams and Validation: The voicemail from an idol symbolizes the culmination of a childhood dream and proof that putting yourself out there can yield rewards.
  • Identity Formation: Tom's struggle with his own white identity as he embraces Black music, sports, and comedy is a recurring motif. His "Black voice" and the comment about being "oddly urban" highlight the tension.
  • The Power of Storytelling: Sharing the Big Daddy Kane encounter onstage eventually leads to the real meeting, turning a funny story into a life event.

Why This Chapter Matters

This chapter provides essential context for Tom Segura's comedic voice and perspective. It explains his influences and his relationship with race, which often surfaces in his material. The chapter also reinforces the book's overarching theme of pursuing unconventional dreams and the rewards of persistence. It is a turning point where a childhood fantasy becomes reality.

Study Questions and Answers

1. What event triggers the narrative of Chapter 5?
Tom Segura receives a voicemail from Big Daddy Kane on August 17, 2014. This voicemail leads him to reflect on his lifelong love of hip-hop and Black culture.

2. How did Tom try to emulate hip-hop culture as a child?
He went to the library to read a book with a glossary of slang, then wrote his own rap rhymes. He performed them for anyone who would listen, using terms like "word" incorrectly, confusing his mother and others.

3. What was Tom's early stand-up style, and how did it change?
He spent his first two years doing a direct imitation of Chris Rock – pacing, crouching, gesturing. A couple told him he seemed "oddly urban," which made him aware of his unconscious mimicry. Over time he developed his own voice.

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