♪ this is "nightline." >> tonight, diplomacy with a dictator. after the funeral of otto warmbier, an american detained by north korea, we're with an unlikely and unofficial envoy to the brutal regime. >> i'm going over there out of the kindness of my heart just to try to help. what'd i do that's so bad? >> did the former nba star play a role in his release? and a chilling warning from a fellow traveler. >> two guards took him away, and that was the last time anyone saw him. plus can't stop, won't stop, a bad boy story. the man whose record label released "mo money mo problems" has become the most successful

hip-hop entrepreneur in history. now diddy's speaking out about his meteoric rise. >> we understood what it would take to make our dreams come true. >> and the murder of his friend, the notorious b.i.g. and rough on the eyes? the competition is frightful at the world's ugliest dog contest. a look at the top contenders and the winner with a face only an owner could love. but first, the "nightline" 5.

good evening and thank you for joining us. i'm rebecca jarvis. tonight we hear from former nba star dennis rodman on why he calls north korean dictator kim jong un his friend. rodman last visited the closed-off country the same day american otto warmbier, held by the brutal regime for 17 months, was released to his family. rodman's team says that was no coincidence. tonight we explore the seemingly bizarre relationship between the despot and the basketball star. and learn more about otto, who died with severe brain damage just days after returning to the u.s. here's abc's bob woodruff. >> as we prepare to leave wyoming hospital, it feels like saying good-bye to a close friend. >> reporter: they're the

prophetic words of the late otto warmbier, saying a final good-bye to his graduating class. >> but also a different kind of good-bye, a farewell to something larger than just a friend. >> reporter: just four years later at that same high school it would be his family and friends who would bid him farewell. >> he was just like full of eternal optimism and hope. >> i think he is a gift to all of us. he was one of a kind. he inspired us all. >> reporter: mourners paying their respects to the 22-year-old whose promise seemed limitless. >> to now have the opportunity to explain what type of a guy he was and what he meant to us, each one of us, we're just cause he was just the best gu >> reporter: on display at the funeral, the quiet testimonies of otto's belongings. shoes, his wallet, his passport. relics of a journey that began with hope and ended in horror. >> it's just unacceptable and unthinkable. >> it's a nightmare, really. >> reporter: thousands in

attendance, all trying to make sense of what happened to the american tourist who for 17 months was detained in north korea. this video sparking a series of events that ended with this college junior losing his life. north korean officials say this is the then 21-year-old allegedly attempting to steal a propaganda poster from a hotel in pyongyang. >> at the airport me and otto were the last two through security. and he simply had a tap on the shoulder. >> reporter: danny graddon was otto's roommate during the trip. >> two guards took him away and i sort of laughingly said to him, well, that's the last we'll ever see of you. and because we got on so well, otto turned around and just chuckled at me. >> reporter: gratton says that was the last time he saw otto. >> please save my life. please think of my family. >> reporter: what followed was otto's tearful so-called confession and a sentence to 15

years of hard labor. a 17-month saga that would eventually bring him back to u.s. soil. north korea claims otto had fallen into a coma. but american doctors say it was unresponsive wakefulness. otto suffering from extensive loss of brain tissue, unable to walk, talk, or respond to verbal commands. >> i'm able to talk to you on otto's behalf, and i'm able to wear the jacket that he wore when he gave his confession. >> reporter: on monday night otto passed away. his family alleging he endured torture that led to his death. but today north korean officials deny they cruelly treated or tortured otto saying "we provided him with medical treatment and care with all sincerity of a humanitarian basis until his return to the u.s." the mystery behind his death adding to the already tense situation between the united

states and north korea. negotiations to free american prisoners have mostly been kept under wraps, leaving a selective few with rare access into the kim jong un regime. individuals like former nba player dennis rodman, who has become the united states' most visible unofficial diplomatic presence. >> sort of open the door. open the door. that's it. >> reporter: last week rodman made his fifth visit to north korea. the same day he arrived otto was released. >> i think i was the one that was supposed to go over there and get him out. >> reporter: rodman and his agent, chris volo, who accompanied the former nba player on his trip, sat down with abc's michael strahan for the first interview since their return. >> otto warmbier was released the same day that you went to north korea. >> give all the prayer and love to his family, you know. but i didn't know that he was sick. >> but he wasn't sick. when he went there, he was fine. a year later the same day you go over he's released in a coma and he passes away less than a week

later. and this -- but this is in a place that you say this guy who runs this place is your friend. how can that happen and you still have these feelings and sentiment? >> -- oh, my god, this guy, my friend, i would die for him, it's not like that. i don't look at the political side -- >> do you think being there had something to do with it? >> i know being there had something to do with it because when i was organizing the trip and i meetith the delegates here i addressed otto warmbier and i said to them we would need some type of good faith if we're ever going to do some type of future sports relation. i asked three times -- >> before you went. >> before we went i asked on behalf of dennis for his release. they said they understood. that was all that was said in that meeting. >> the same day you go in he's released. do you look at that and think maybe we're being used here, maybe we're a distraction from that? >> you know, i have, but there's

no doubt in my mind that these trips and me asking on his behalf was the -- had a lot to do with it. >> otto's father said -- >> dennis rodman had nothing to do with otto. it's a diversion. you know, they just released otto. it's a diversion. >> we wanted to meet with him when we came back. you know, but we were told that it just couldn't happen. >> have you talked to anybody there and said what happened with this kid? >> no. we haven't heard anything. >> but it's just mysterious, dennis. a 21-year-old healthy kid, all of a sudden he's in a coma. that's not normal. something apparently happened. no one wants to say what happened. but something happened. >> i'm not into all that. like i said, i was just so happy to see the kid released. laterhat day, thas when we found out he was ill. no one knew that. i was just so happy, said oh, he got released. i was jumping up and down. all right, man. all right. good things came out of this trip. okay, great. >> so with three more americans being held over there, are you going to lobby for their release as well? >> if we could get more trips going over there i think

anything is possible. >> it's possible. >> why did both of you do something that's so controversial -- >> i'm like a controversial person. i love it. controversy means bad, negative, and good publicity for everybody in the world. people today would do anything on tv just to be on >> is that part of your motivation, to be on tv? >> i donate need to be on tv. i'm too damn famous for this. i'm not trying to sound cocky. i'm like my god, what am i getting out of this? i'm going over there out of the kindness of my heart just to try to help. and next thing i know i come back, wow, what did i do that's so bad? i'm not sitting here to say i've got to be -- >> with that being said and seeing you get emotional, do you think these trips you've taken have been worth all the criticism? >> absolutely. >> i think it's worth it. >> reporter: the state department sees his involvement

differently. >> dennis rodman had nothing to do with the release of mr. warmbier. >> reporter: otto is not the only american being held in north korea. secretary tillerson this week has demanded the return of three american prisoners who remain in the country. governor bill richardson, who runs a foundation aimed at rescuing political prisoners -- >> so nice to see you. >> reporter: -- personay met with the north koreans to free otto. >> the north koreans stiffed me. they never said yes. they never said no. otto was in a coma, and they didn't want anybody to know. >> reporter: the former governor has a stern warning to the estimated 1,000 americans traveling to north korea every year. >> don't go to north korea if you're an american tourist. you don't need to go there. go somewhere else. it's too dangerous. and you may end up like otto warmbier. unjustly killed. this is a human being detained, 21 years old, with a great family, a grieving family. north korea should not get away with this. >> reporter: and as america

mourns otto's death -- >> i wish there was a way to know that you're in the good old days before you've actually left them. >> reporter: back at his high school his friends remember his bright spirit. >> he said we'll always have each other talking about our class. and i think now more than ever that's really showing to be true. and otto would want that. >> the memories we've created to be played over and over again. thank you. [ applause ] >> reporter: for "nightline" i'm bob woodruff in new york. ♪ next -- ♪ don't push us can't nobody hold me down. rapper diddy on the rise of his bad boy crew. ♪ not to lose our heads later, there are good dogs, bad dogs, and these dogs. we're on the scene of the world's ugliest dog competition. . ...better than a manual, and my hygienist says it does. but... ...they're not all the same. turns out, they're really... ...different. who knew? i had no idea. so, she said look for...

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hip-hop mogul sean "diddy" combs was on the scene of one of the most high-profile rapper assassinations in history. he launched a record label that dominated the charts and redefined the rap genre. along with a clothing line and a cable channel. if you're thinking someone should really make a documentary about his life, he's already beat you to it. here's abc's michael strahan. >> reporter: he's gone by many names. >> puff! >> reporter: but there's only one. >> p. diddy! >> reporter: sean "diddy" combs. responsible for launching some of the biggest names in hip-hop, including his late friend christopher wallace, aka notorious b.i.g.

>> police investigated the deadly wilshire boulevard ambush of notorious b.i.g. >> reporter: biggie's death leaving a mark on family, friends, and the man behind the music. ♪ i know you still as seen in the iconic 1997 tribute "i'll be missing you." ♪ every move i make ♪ every single day ♪ every time i pray ♪ i'll be missing you >> it made me appreciate life, and it made me want to be -- do things for the great yef good. >> how do you carry on his legacy? >> i wanted to make sure this dream meant something at the end of the day because this young man, you know, lost his life throughout this journey. >> soon as them shots went off everything came crashing down. >> reporter: that legendary loss and the rise of bad boy records explored in a new documentary "can't stop, won't stop: a bad boy story."

>> what is the bad boy story? >> the bad boy story is a group of young individuals that have come from the new york area that grew up and was influenced in hip-hop and took hip-hop to another level. >> reporter: the label which combs founded in 1993 changed the music industry forever. >> we dominated hip-hop and r&b and really changed the -- really the platform of radio. we were making so much hip-hop and r&b that they had to start dedicating stations to it. >> reporter: hit after hit from lil' kim's first single "no time." lose control ♪ to that unforgettable "mo money mo problems" music video. ♪ ♪ the more money we come upon the more problems we see ♪ >> why did you want to do a documentary? >> it started out as something we were going to do that was really centered around us all coming back together because we all started together and we were successful not just because we were great individually but because of what we meant

together. and as we're shooting the documentary, you start to see this other story develop about growth and family and perseverance. it kind of gives you the true story and lets you see the behind the scenes of my real drive and what fuels me. and really kind of like the man i really am off of puff daddy. >> reporter: combs' drive, unstoppable. >> i don't want the chrysler that looks like the fant movement. i want the fantom. >> reporter: the documentary that premiered at the 2017 tribeca film festival also looks at combs' incredibly high standards. >> if it don't sound just like the record it's just wasting time. it's never going to fly. >> reporter: and the talent he brings together on stage and off. >> you have to fix your energy. that's not -- you have to fix you are energy. that's all i'm asking out of respect. >> reporter: as he tries to reunite the bad boy family.

faith evans, lil' kim, mace and others for an explosive anniversary concert. ♪ combs using the bad boy label to amass a lifestyle and an empire. >> what was your vision when you started bad boy? >> i think i had the confidence because of berry gordy, russell simmons and andre harrell. so i was standing on the shoulders of giants that had already started to create this lifestyle and this culture. i had this dream that i would help create your lifestyle. >> full service. >> reporter: a lifestyle that paid off. combs is the most successful hip-hop entrepreneur in history, with a net worth of $820 million according to "forbes." in addition to his various brands, combs dedicates his time to his six children. what are you teaching them? >> i'm just making them come with me so they can see and live it hands on, just really making sure that they're involved and they're working. >> reporter: his oldest son justin recently granted ucla on a football scholarship. >> he wants to run the company.

and so he's with me. and that's the fulfilling thing. these are my kids as far as by blood. but then i have millions of kids all over the world that i want to make sure that i mentor through being an example of what i do in business and aspire to people that need, especially need the inspiration. >> reporter: what is one piece of advice or anything you think you can say to inspire them to chase those dreams? >> i want to make sure that i could do anything i can to provide the infrastructure to make sure people get educated. you can't rise in this game if you don't have the education. and right now it's not set up for our people to rise. >> reporter: combs doing what he can to help. opening up a charter school in 2016, capital preparatory in harlem. and it's that can't stop won't stop mentality that inspires people every day, just like his music. what do you think is the legacy of bad boy? >> i think the legacy is in the music. we made so many people dance and so many people feel good through

the music. and that was the intentions. at the end of the day i was saying only the song survives. >> reporter: for "nightline" i'm michael strahan in new york. next, it's the world's ugliest dog competition. will rascal or josie take home the top spot? or could it be moe? more "doing chores for dad" per roll more "earning something you love" per roll bounty is more absorbent, so the roll can last 50% longer... ...than the leading ordinary brand. so you get more "life" per roll. bounty, the quicker picker upper and now try bounty with new despicable me 3 prints. in theaters june 30.

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and finally tonight, before you judge these dogs, remember beauty is in the eye of the leash holder. >> reporter: today they fought, snaggletooth and nail, for the coveted title of world's ugliest dog, to be crowned here at the sonoma marin fair in northern california. >> i don't want to say that icky and john look alike, but icky and john look alike. >> reporter: the prize, 1500 bucks in cash and an all expenses paid trip for dog and owners to new york. for a media tour. last year's winner, sweepea rambo. oh, my. 2015, quasimodo.

i was a guest judge that year. >> ugly, ugly, ugly. this dog has attitude as well. ugly on the inside. >> reporter: peanut won the year before. inner beauty, people. inner beauty. this year's bronze chase. drooly, lovable neapolitan mastiff named martha. >> absolutely a tremendous honor. she's a dog we took in as a rescue. we think she's beautiful. but we thought you know, i wonder. >> reporter: i'm nick watt for "nightline" in los angeles. >> i think they're all kind of cute. thanks for watching abc news. and as always, we're online at