Entering the gates to the residence of the United States ambassador to Singapore, Mr Kirk Wagar, the American flag flies high as we drop at the spartan porch. The rest of the residence is tastefully furnished: no overt signs of opulence, just a few books on Muhammad Ali and a painting of the American flag in candy-like colours and swift strokes of acrylic.

“If you can make me look thin…” Wagar remarks as he saunters into the living quarters that Friday afternoon and spots our video camera set-up. Wagar’s spirit is infectious and he does wear his enthusiasm on his sleeve — or rather, on his yellow and sky-blue striped socks.

The enthusiasm does indeed match up to his past: Wagar raked in more than $1 million as finance chair for US president Barack Obama’s re-election campaign in 2012, supporting Obama early on even as many tipped Hillary Clinton to be the Democrat representative in 2008.

And that passion shows when Wagar talks about the inaugural Joseph Balestier Award for the Freedom of Art that the US Embassy in Singapore is giving out as part of trade fair Art Stage Singapore. Seven artists from the South-East Asian region who espouse freedom of expression and liberty have been nominated, including one from Singapore (Lee Wen). The winner will be awarded January 20 at the ambassador’s residence with a US$5,000 grant along with a trophy and certificate.

In Part 1 of our sit-down interview with Wagar, he talks about the motive behind celebrating freedom and struggle, and the “sheer thievery” that the recent Sony hackings caused to the freedom to create:

In Part 2, Wagar talks about how Singapore is the gateway to ASEAN and not many countries have realised that yet:

Wagar believes it is not in the place of the United States to go to other countries and correct their state of freedoms, including Singapore. Show the merit of being open — that is what Wagar believes America should do in its dealings with others.

As we wrap up, we went back to the question the man with over 8,000 songs in his iTunes library might find difficult to answer: what’s his iPod song obsession? Without a beat, he referred to the old-school hip-hop tunes from a band named A Tribe Called Quest. (You may recognise Q-Tip in this band.)

In “Check The Rhime”, Q-Tip raps, “How far must I go to gain respect? Um/Well, it’s kind of simple, just remain your own/or you’ll be crazy, sad and alone”.

Exactly the tactic one uses to stay true to one’s values.

Singapore Art Week continues until January 25. Art Stage Singapore shows January 22 to 25 at Marina Bay Sands.