Timothy Olyphant

Olyphant described his technique over the past decade as memorizing lines to exhaustion.

“my technique for the last decade or so has been memorizing the lines and then memorizing them to exhaustion so I show up hopefully in that place”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 51:52

Olyphant argued the flip side as well: the best comedic performances are really dramatic.

“flip side, which is the best comedic performances are really dramatic”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 19:06

Olyphant said sitting beside Margo Martindale when she won an Emmy was the first time he understood what awards meant.

“when they said her name, she squeezed my hand like it could have bruised me”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 38:56

Olyphant recounted asking Eric Roberts on the Justified set how often he had been arrested, and Roberts said in the double digits.

“I said to him, I asked him... how many times have you been arrested? And he said something like in the double digits”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 7:55

Olyphant said he does not own a working computer and had to dig out an old desktop, then used someone's office, to record the podcast.

“We went, I had a, we went and got out a old desktop computer that we still have in the house and plugged it in”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 33:18

Olyphant said he pursued acting partly to head off a midlife crisis like the one he saw his father go through.

“I do think I had a certain amount of conscious thinking that I was wanting to put off a midlife crisis”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 28:23

Olyphant said David Fincher's many takes make it hard to ignore the inner voice saying you are doing it wrong.

“you're doing it so many times, it's hard to shut out the voice that feels like you're doing it wrong”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 50:41

Olyphant said Steven Soderbergh gave him no notes over three months, with one exchange rating a take.

“On a scale of one to 10, that was a seven, maybe an eight. And I was like, all right, cool”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 45:19

Olyphant recounted that David Milch, after an off-set dispute over a child actor, decided to kill the character, which became the season's storyline.

“there was a knock on my trailer door, and I open, it's David, which is unusual, and I said, what's up? And he says, we're gonna kill the kid”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 40:38

Olyphant said that no one prepares a stand-up comic for the silence on stepping out before saying a word.

“this thing that no one prepares you for when you do standup, which is the moment you step on the silence”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 30:08

Olyphant said students with a Bachelor of Fine Arts have many career directions open and are attractive to employers because of their creativity.

“If kids who get like a Bachelor of Fine Arts, they just still have so many different directions they can go”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 27:13

Olyphant argued that De Niro was aware of the comedy in even his most dramatic roles.

“De Niro knew he was being funny in those roles, even the most dramatic roles”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 18:15

Olyphant joked that, now an empty nester, he would not have grown so close to his children if he did it again.

“So they just leave you. So just so you know. Like if I did it again, I wouldn't have gotten so close”

SmartLess: "Timothy Olyphant" (Jul 20, 2026) · Listen from 12:01