Andy Daly Played Andy Richter’s Sister’s Boyfriend On "Late Night" | Conan O'Brien Needs A Friend

when I graduated college in ' 85 I. desperately wanted to do improv and the. only place I thought you could do improv. in the United. States was in Chicago Second City or. impr Olympic all I knew about was Second. City so I wrote a letter to Second City. I did that too and it was like dear. s you know or Madam you know it was just. like I would I wish to do this improv uh. you know my name is Conan O'Brien I just. completed my communic studies at the.

Lampoon and I think I'm now and I've. done some performing I would like to. join you and of course that's not how. you do it and I just got a form letter. back saying um uh go away and um and uh. but also I couldn't go to Chicago. because I I got a gig in La so I went to. LA and uh eventually found would didn't. take too long but I found improv there. which was the Groundlings theater but. years later the Upright Citizens Brigade. I guess started in Chicago used to be MH.

and um and then came. to New York and all these brilliant. people suddenly and we we we were the. benefactors when I say we I mean the. people that worked with me on The Late. Night show we were the benefactors. because all these incredible performers. showed up yeah who had amazing chops and. uh I actually kind of preferred their. style of improv I thought it was really. pure and great and I know that you were. part of that yeah well can I just say my.

letter to Second City was so. embarrassing because I had just. graduated from college and I I had read. in wired the book about John balushi. that he did an impression of Mayor daily. that was so popular that the audience. would chant daily daily and so I made. some mention in my letter to perhaps one. day the audience will be chanting that. again that's sweet and so you. immediately got a job based on that but. I did get my form letter said well we. have uh our annual audition coming up. you come up here and I somehow.

interpreted that as like a really like a. personal invitation to come up in. audition all the indications were there. that it was not yeah but uh I did I. scheduled an audition and and I had no. idea what was like uh people everybody. else auditioning had been through the. classes and had auditioned before and. was steeped in this world and I just. showed up like I'm here to get a job. yeah did not go well you had a suitcase. with lots of stickers St. Louis yeah exactly but uh no they they. suggested that I should take glasses but.

was I was living in New York and I. stayed in New York and then yeah it felt. like Chicago came to me in 1996 showed. up and what an amazing group of people. and we were fortunate I've mentioned. this before but Amy po was with UCB and. so we cast her as Andy's little sister. yeah who had a crush on me and she has. like a big uh retainer you know uh. headgear I was in a bit one of those. bits as her boyfriend that's right so. tell me how that worked because her. thing was always always that she was.

pining for me and she would stand up. interrupt the show and then Andy would. always have to break it to her that you. know this isn't appropriate or something. and she would suddenly. turn and God I mean I remember Amy po. could take we thought gave her good. scripts and she could take whatever we. gave her let's say we gave her a solid b. or B+ script she would turn it into an. A++ Plus+ plus but she would turn and. she would summon the the Devils from the. deepest ows of Hell to rain down upon us.

well the amazing thing about those bits. too is when you do a Conan bit in those. days you if you were on the stage you. could have q cards but if you were an. audience plant there weren't Q cards. because they didn't want the studio. audience to get ahead and and read with. you so you had to memorize it which is. unreasonable but so Amy had those. speeches memorized completely memorized. and committed to them like 110%.

and that was very like instructive and. inspiring to me to watch that because I. had comparatively very little to say but. the incredible things that she was doing. but so that bit was like uh she brought. along her boyfriend to try to make you. jealous basically and then when it. didn't work she just you know throws me. under the bus. completely and goes into her angry TI. raade well we uh well so we also. benefited by having you and then you uh. I think you did on my last late night. show which is 3 years ago today I don't.

know when this airs really actually this. isn't never going to air um no no this. is just you got a very bad. diagnosis this is to cheer me up this is. like a make a wish thing yeah and even. you're not aware that you're ill. but that would be a better way to do it. yeah now your wife just asked you know. so anyway uh we. um uh you came on and you did something. I think the on the last show yeah and uh. I remember just stopping you I wouldn't.

let you leave I was like ladies and. gentlemen this guy Andy Daly is the. funniest person uh walking the Earth and. uh yes I and I was as uncomfortable then. as I am now I don't really mean it I say. that helps that's helpful yeah I said. that to everyone okay we just had JLo. here I said you the funniest person to. ever walk the earth she just glared at. me. angrily um so so you do improv and. somewhere along the line you got this.

conviction because when I listen to your. monologues and you tell these stories. you did another one as a leprechaun do. you do one as a leprechaun it's um an. Irish Storyteller tells stories about. leprechaun he tells stories about. leprechauns and um God it's so dark but. you just go into it with such full. commitment and you never wink you never. break uh and it's just a testament to. your just conviction that this is what.

I'm doing mhm and it is 100% right yeah. and anyone who disagrees can leave which. just I don't know I love that I think. that's the way you have to go yeah I. always felt annoyed when the host of the. show after I left would go Andy daily. ladies and gentlemen I like no leave. them thinking it's patio. hurle so what is what was the gag with. patio hurle because I remember it was. really funny he's an he's an Irish. Storyteller who talks about leprechauns. but he gets sidetracked doesn't he I've. changed it a B I think the one on the. album is that he's um he's won a Blarney.

contest so this is like whoever can tell. the most Fantastical stories about. leprechauns and and harpies and whatever. wins the Blarney contest and he's a. wonderful Storyteller and so he tells. the audience what his sto it's something. like I showed up for Christmas lunch and. I was full and I couldn't eat a bite and. somebody said Patty why are you showing. up for Christmas lunch and you can't eat. a bite and I told and then he weaves a. whole story about leprechaun and. whatever and then he says now but what. really happened was and then he tells.

what really happened which is like well. there was a I'm I'm a landlord and this. this woman didn't pay her rent for the. longest time and I says to her you got. to pay that rent and she says no. I don't have it I don't have it and I. says well you know what I'll do then I'm. going to kill your cat and put it in a. stew and eat that right in front of you. and that's what I did I AER. cat and then I remember him going like. he does a transitional thing where he. goes like so I don't know what it is. like the equivalent of so anyway I. forget what it was but it was really. funny like a.

well right every Story begins well it. seems one day yeah something like that. really. hilarious how do people get though the. how can you hear all those monologues. are they available well they're all. collected on an album called Nine. sweaters and that I think is on your. streaming things like you you can find. it on your Spotify find it's if you. really want to laugh these are such. great monologues they're so funny n. sweers find that um I'm going to.

relisten to it cuz I'm always I think. about them every now and then I realize. that I got it no I don't have it right I. have to listen to them again I'd like. you to memorize them I'm going to. memorize them yeah after because you. guys you guys had to memorize stuff for. me all those years yeah ex I had two. cards yeah right you never ventured into. the. audience those awful people I'm not. going to go in there every now and then. people would say con why don't you drift. in the audience and and talk to.

them the filthy weirdos who come to this. show who would come to this show if they. didn't have to they're just here for. free sandwiches I suppose.