Chris Gardner, the character portrayed by Will Smith in the movie "The Pursuit of Happyness," is interviewed by 20/20 (it is broken down into a Part 1 and a Part 2).
The lesson provides links to the two videos, and contains eleven (11) higher level discussion questions that will engage students.
I used this in my "The American Dream" unit. In this unit, my students study informational text about homelessness in America, we watch the movie "The Pursuit of Happyness," read "Sharing in the American Dream" by Colin Powell, read "A Dream Deferred" by Langston Hughes, and watch this interview with Chris Gardner.
In the past, I have had the students draw numbers to partner up, where each couple has a different question. Then, the students share and we discuss the answers. Of course, you can implement the questions however you'd like.