David Letterman said he didn't expect to be hit so hard emotionally after he dropped his 18-year-old son Harry off at college on Tuesday's episode of Jimmy Kimmel Live.
The 75-year-old former talk show host wore a black suit and sported a full beard as he opened up about the milestone on the ABC talk show from its set in Brooklyn.
'The separation of the kid leaving home I thought it would be nothing but it's devastating,' Letterman said. 'Am I the only one that feels that way?'
Letterman described what it was like when he dropped Harry off at college.
'He's been gone a month today,' he said. ' We had a truckload of crap to take up to his room and his room man, it's not as big as the desk.'
Letterman said they found a place to park the truck 'several acres away.'
'Ninety-six degrees and then the kid and I carry his stuff up three flights of stairs,' he said.
Letterman said he called him a week later to see how things were going.
'I said ''Harry have you met the kid yet that sells weed?''.' David said. 'I'm thinking this would get a good laugh. Harry says, ''I cannot confirm or deny''.'
Letterman also thanked Kimmel, 54, for having him on his show.
'It's nice to see you but mostly it's nice to be on TV, thank you for that,' Letterman quipped.
The talk show veterans discussed their mutual friendship with Howard Stern, 68.
'I feel Howard Stern is threatened by you,' Kimmel said. 'I feel Howard is jealous of my admiration for you.'
Letterman said 30 years ago that he used to work in the same building with Howard.
'In those days, Howard was 'Shock Jock Howard,' Letterman said. 'I was always afraid of Howard. Because I didn't want Howard to say unpleasant things about me but he did. I kept thinking, he must not have any feelings of his own because he would say hurtful things and the more hurtful things he would say the greater his audience would become.'
Letterman said over the years he has spent time with Stern and got to know him.
'He was such a sweet man to apologize for intimidating me,' Letterman said. 'It was ''I'm sorry if I frightened you'' and I got to know him as a completely different guy. And that's the guy that I have really gotten to be friends with over the years.'
Letterman said he only talks to him once a year.
'That's plenty,' Letterman added. 'And the last time it was a mistake.'
The comedian said his phone lit up and it was a photo of one of Stern's paintings. Letterman said he immediately texted him and later called Stern to tell him the picture was unbelievable.
'And he says ''Oh, yeah, I sent that to you by mistake'',' David said. 'I love Howard. I just think maybe arms length may be the way to go here.'
Kimmel then played a clip of Letterman questioning basketball player Kevin Durant from his new Netflix series My Next Guest Needs No Introduction.
'Kevin is an amazing athlete and an amazing human, fascinating, and he's always high,' Letterman joked. 'He told me that the first thing he does when he gets out of bed is he lights up a joint and then he's in business. I thought, well it's like I have a twin.'
Letterman said after filming he went up to Kevin and said he wanted them to remain friends.
'He said ''yup, I agree,'' and we hugged,' Letterman said.
Letterman revealed that he texted Durant on opening night when he was playing the Celtics in Boston and before tip-off he texted him to wish him good luck.
'After the game is over, I get a text back and it says 'thanks bro,' Letterman said. 'I haven't heard from him since. But how cool would that be if Kevin Durant and I were hanging around.'
Kimmel said when Letterman did a show in Vegas that he wrote 20 letters to the show asking for tickets and that he went to every one of his shows. He said it was now delightful to have Letterman on his show.
'I don't mean to be harsh but you understand, from my point of view, there may be an element of this that sounds creepy,' Letterman said.
'You didn't do this with Johnny?' Kimmel asked, referencing late talk show host Johnny Carson.
'Oh no. Johnny scared the crap out of me,' Letterman said. 'I will say that over the years, and it has been years, no one in show business has been kinder to me than Jimmy Kimmel.'
