Years before you got your role on “The League,” you were a talking head on various VH1 pop-culture shows. Did comedians get paid or was that cable TV slavery?

“Best Week Ever” paid; other VH1 shows I did, like “Awesomely Bad Metal Songs” and stuff like that, we did for free. The difference between slavery and being on VH1 is that we signed a release.

Image Nick Kroll Credit... Ricardo Pinzon for The New York Times

Did you hate them for that?

There’s so much free work in comedy, you just accept it early on.

I was surprised when one of the repulsive jerks in your recurring sketch about two drug-addled trust-funders is revealed to be H.I.V.-positive and it’s played for laughs.

That was written on a hike. We thought it would be hilarious if Wendy was living with AIDS.

What’s hilarious about living with AIDS?

In general, it’s not hilarious at all; but how flippant for a rich kid, that something like H.I.V. is just a small speed bump. His living with H.I.V. is no different than the annoyance of his car getting towed. It’s just an extra 15 minutes in his day.

You’re not afraid of portraying black characters, like Fabrice Fabrice, a flamboyant craft-services coordinator. Are there questions you ask yourself to avoid being accused of racism?

If I do a black character, then it’s likely it will seem as if I’m doing blackface. In reality I’m like, How is that different from me doing an older Upper West Side Jewish guy or a Latin radio host or an overprivileged rich kid or a Guido? But it’s tricky. Fabrice, by the way, is possibly Blatino and based on tough kids I used to watch on Christopher Street, whom I just marveled at.

Your father started the private-investigation firm Kroll Inc., his share of which he sold in 2004 for about $100 million. Do you think coming from that kind of wealth helped you in your career?

It helped me to look at how my dad ran a business. Whether it’s corporate investigations or comedy, there are certain inherent truths to trying to get what you want while trying to be a decent person doing it.