If you can make it here...
  1. Mayor
  2. Woody Allen's chaffeur
  3. Conductor of NY Philharmonic
  4. Beyonce's trainer
  5. Head of Security, Yankee Stadium
  6. Head of Security, Freedom Tower
  7. Lead Curator, MOMA
  8. Costume Designer, SNL
  9. Point Guard, New York Knicks
  10. House Drummer, Village Vanguard
  11. House Drummer, Tonight Show
  12. Actor with Second Billing on a Broadway Show
  13. Photo Editor, NYMag
  14. Restaurant Critic, NYTimes
  15. Bill Cunningham
  16. Concierge, Carlyle Hotel
    Suggested by @bjnovak
  17. Head of NYC Parks and Rec
    Suggested by @jilianbream
  18. The original Naked Cowboy
    Suggested by @jilianbream