"WGN is the ultimate in randomness."

1. The following list is not exhaustive:
Randy Pausch -> Katie Couric
Brad Pitt & Angelina Jolie -> George Clooney
George Clooney -> Roseanne Barr
Chris Rock -> Jerry Seinfeld
Indra Nooyi -> Howard Schultz
John McCain -> Joe Lieberman
Hu Jintao -> Henry Kissinger
Sonia Gandhi -> Shashi Tharoor
Oprah Winfrey -> Michelle Obama
Andre Agassi -> Andy Roddick
Carlos Slim -> Alvin Toffler
Kaka -> Kasey Keller
Tony Blair -> Bill Clinton
Susan Solomon -> Rajendra Pachauri
Dalai Lama -> Deepak Chopra
Vladimir Putin -> Madeleine Albright
Miley Cyrus -> Donny Osmond
Bruce Springsteen -> Sean Penn
George W. Bush -> Silvio Berlusconi
Mariah Carey -> Stevie Wonder
Khaled Hosseini -> Laura Bush
Suze Orman -> Donny Deutsch
Steve Ballmer -> Guy Kawasaki

Explain.

Hint: The people on the left are the people on the list.

Answer:
The people on the left feature on TIME magazine's 100 Most Influential People in the World. The people on the right have written the TIME 100 articles for the corresponding people on the left.
2.










These are the first three (in order from left to right). Give me the fourth and the fifth.

Answer: Indira Gandhi & Sonia Gandhi - Women Presidents of the INC. (Annie Besant, Sarojini Naidu, Nelli Sengupta - left to right)
3.















Sitter. Identify.

Answer: Oscar Pistorius
Image Source: TIME 100 Most Influential People in the World