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Get ready to dive into some of the most unforgettable moments shared between legendary musicians and their interviewers. From raw honesty to unexpected outbursts, these iconic conversations reveal the personalities behind the music. Whether it’s John Lennon’s peaceful Bed-In or Eminem’s reflective sit-down, these interviews shed light on the artists’ lives, careers, and groundbreaking influence, making music history come alive like never before.
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00:00Welcome to WatchMojo, and today we're counting down our picks for the most memorable, famous, and or impactful interviews of
00:07musical artists.
00:08I'm never pleased with anything. I'm a perfectionist.
00:12Number 20. R.E.M. Reunite and Support Each Other. CBS Mornings.
00:17As one of the most important bands of the 1980s, R.E.M. was inducted into the Songwriters Hall of
00:22Fame for their career.
00:23In this interview, the original quartet talked about their catalog and their overall musical process.
00:28Once we realized we could, it was like the keys to the kingdom.
00:33Once we realized that we could actually sit down and create these things, then we could play them for people
00:38and lift everybody up. It was magic.
00:41This included a discussion about their growth as artists and their ability to share songwriting credit.
00:47With the latter point in mind, it's clear that these guys have a special and unbreakable bond.
00:51Drummer Bill Berry describes his feelings about stepping away from the band, but his bandmates quickly comfort him in a
00:56tearful moment.
00:57You okay?
00:58Yeah. That was a weird time for me.
01:01I bet.
01:02And I made it weird for these guys, too.
01:04No, it wasn't weird. We respected your decision 100%.
01:08Their supportive energy seems especially rare in such a cutthroat industry.
01:11As a portrait of great artists and humans, this interview feels like the cap to an awesome, multi-decade career.
01:19Number 19. Harry Reasoner Interviews Johnny Cash. 60 Minutes.
01:24The man in black created his own persona that transcended country music.
01:28In this 1982 interview, Johnny Cash peels back the curtain to reveal his thoughts about his tour and life as
01:34a musician.
01:34When you were on The Pills, did you think you were a better singer because of him?
01:38I thought I was invincible.
01:42I thought I was indestructible.
01:44It's a more laid-back version of Cash than some people might expect.
01:47Beyond the classic hits and murder ballads, the singer is an ordinary man hoping to do right by his audience.
01:53Even though he's worked through many struggles, he shows his trademark charm in this CBS exclusive.
01:58Plenty of people might prefer his darker side, but this exchange lets people into a much more inviting side of
02:04an American original.
02:05Roy Orbison had a line in his song called My Best Friend, and then it was a line that says,
02:11A diamond is a diamond, and a stone is a stone, but man is part good and part bad.
02:18You know, I recognize the fact that I'm part good and part bad.
02:22If you're eager for more of The Man in Black, head over to WatchMojo's 24-7 livestream
02:26for more famous moments from music history.
02:29Scan the QR code on screen to join us for the latest in all things music, past and present.
02:33The songs you've written, what's your favorite, Connor?
02:37Well, I think I probably should say I Walked the Line because it was my biggest seller.
02:42But the one that really means more to me, that says it more for me in my life, I think
02:48is Picking Time.
02:49Number 18.
02:51Barbara Walters Interviews Courtney Love.
02:53Barbara Walters' 10 Most Fascinating People.
02:55In the middle of the 1990s, Courtney Love found herself at a crossroads.
03:00She was reeling from the death of her husband, Kurt Cobain, and under increased scrutiny as a single mother.
03:05Are you a good mother?
03:07Yes, I'm an excellent mother.
03:09Not only that, her history with substances led many to speculate about her future.
03:13Barbara Walters discussed many of these topics during an interview in 1995.
03:17Love seemed eager to explain herself, becoming an open book for Walters during a troubling time in her life.
03:22This also marked a new period of success for her as an actress and a member of Hull.
03:27I couldn't have gotten anywhere if I wasn't good.
03:29You know, you wouldn't be talking to me right now if we actually sucked.
03:35Finding this musician at a vulnerable moment, the interviewer dove headfirst into personal drama.
03:40Number 17.
03:41Jay-Z announces his retirement.
03:44106 and Park.
03:45Back in 2003, Jay-Z was on top of the world with hit albums and a coveted career.
03:50He then shocked the world with an announcement about retirement.
03:53Is this gonna happen or is this not happening or what's the deal?
03:56Yeah, that's where I'm at right now.
03:58For an interview on 106 and Park, the rapper clarified his intentions with talk about the Black album.
04:04It seemed like the hip-hop superstar was ending his solo career on top and more interested in mentoring groups
04:09like Young Guns.
04:10This show captured the artist at a turning point, but it didn't prove to be the real end.
04:15Not the last album.
04:16Sorry.
04:16Don't start.
04:17Do a joint.
04:17Retire or come back.
04:18Alright, four years.
04:20He didn't spend long in retirement before returning to the studio and extending his legacy.
04:24With his work in both the music industry and the business world, this segment found an influential figure on the
04:30cusp of his next venture.
04:31Number 16.
04:33Eminem on 60 Minutes.
04:3560 Minutes.
04:36Among the more controversial artists of the 2000s, Eminem certainly developed a reputation as an outspoken rapper.
04:42Anderson Cooper interviewed him in 2010 for 60 Minutes.
04:45The no getting away from fact that I am white, you know, and this is predominantly Black music, you know,
04:52and people telling me you don't belong.
04:54Like, you're not going to succeed because you're this color.
04:57Then you want to show those people that, you know, that you can and you will.
05:01Hoping to find a way through the man's hardened exterior, Cooper set his sights on Eminem as a lyricist and
05:07technician.
05:07Some of these questions give us insight into the mind of a highly successful artist.
05:12While some of his raps might seem aggressive or audacious, the MC shows off his more subdued and thoughtful side
05:18during this interview.
05:19An artist can say that they get used to it, but I think that they're probably lying if they do.
05:24It's rare to see someone known for such heavy lyrics sitting down in a quiet setting to discuss his work.
05:30Number 15. Tupac's BET Interview.
05:33BET.
05:34Few people argue with Tupac Shakur's talent, but some didn't realize the extent of his genius.
05:39His BET interview with Ed Gordon gave audiences another look at the man's articulate vision of both music and society.
05:46I feel like I'm doing God's work, you know what I'm saying? Just because I don't have nothing to pass
05:50around for people to put money in the bucket don't mean I ain't doing God's work.
05:53Shakur talked candidly about real-world issues and problems in American life.
05:58Dealing with heavy subjects, the rapper wasn't afraid to talk about his own fate.
06:02This unfiltered snapshot of the rapper came off the cuff with a natural and poetic streak.
06:07He was able to talk about culture, family, and fame like few others of his generation.
06:12When I come, I don't have to say I'm real. They already know that, you know what I'm saying? For
06:15me, for me being me.
06:17Wise beyond his years, the artist showed his sensitivity and a comprehensive look into his psyche.
06:23Number 14. Bob Dylan on 60 Minutes.
06:2560 Minutes.
06:26How do you interview somebody that's an enigma?
06:29Bob Dylan isn't the easiest subject to question, but he's among the more fascinating artists of the 20th century.
06:35You don't think you can do it today?
06:38Uh-uh.
06:39Does that disappoint you?
06:43Well, you can't do something forever, and I did it once, and I can do other things now, but I
06:51can't do that.
06:52For this 60 Minutes segment, Ed Bradley tries to dispel many myths about Dylan and his songwriting.
06:57Even in his more pensive and withdrawn moments, he does seem to give more insight about his larger pop culture
07:03persona.
07:03In other cases, he clarifies that even he can't quite believe what he achieved at such a young age.
07:09Why do you still do it? Why are you still out here?
07:11Well, it goes back to the destiny thing.
07:14I made a bargain with it, you know, a long time ago, and I'm holding up my hand.
07:21What was your bargain?
07:23To get where I am now.
07:26While the singer might still seem elusive after this questioning, he proves to be as accessible as he's ever been
07:32in a televised interview.
07:33Number 13.
07:35Aaliyah on 106 and Park.
07:37106 and Park.
07:38On the famed show 106 and Park, Aaliyah showed up to talk about her recent string of success in the
07:43early 2000s.
07:45Little did anyone expect this to be one of her last major interviews.
07:48Now, your album has been out since mid-July and it's been doing so well.
07:51We gotta congratulate you on that.
07:53I have to thank all of you guys for that. Thank you.
07:55Full of life and ready to talk, the pop and R&B singer shared a unique perspective on fame during
08:01this segment.
08:02The easygoing interview covered her upcoming releases and even included a Cadillac giveaway.
08:06She achieved so much by the age of 22, but she tragically died in a plane crash less than a
08:11week later.
08:12The beloved vocalist brought such a positive energy to this BET staple, lighting up what became a bittersweet reminder of
08:19her endless charm.
08:20We want to thank you for entering the contest and winning and Aaliyah, thank you for coming through.
08:24No doubt. No doubt. I gotta think BET and I'm just happy for it.
08:27Number 12.
08:28Cher calls Letterman an A-hole.
08:30Late Night with David Letterman.
08:32Harboring some negative feelings about the host, Cher appeared on Late Night with David Letterman during a new phase of
08:37her career.
08:37While she might have played nice on another night, she chose to be blunt with the interviewer during this segment.
08:43Is this as good as it gets?
08:49No, no, we got a lot of great stuff here. Don't worry.
08:52She didn't seem all that interested with Letterman's interview style or brand of humor.
08:57The key moment came when the guest got bleeped, leaving the comedian speechless.
09:01It all ended up as one of the more interesting dynamics on 1980s late night television.
09:05I see how you deal with your guests and sometimes it's really great and you seem to like them and
09:11then sometimes if you don't like them, I mean, you might as well take a picnic lunch, you know?
09:16During her return trips to the show, she seemed in better spirits and opened to joking with the comedian about
09:21their playful dynamic.
09:23Number 11.
09:24Jimi Hendrix on The Dick Cavett Show.
09:26The Dick Cavett Show.
09:27For being one of the best guitarists in the world, Jimi Hendrix was certainly humble about his craft.
09:32He joined The Dick Cavett Show to talk about his recent successes and a performance at Woodstock.
09:37That's what it's all about, you know?
09:39Yeah.
09:39It's a show.
09:41Try to keep violence down, you know, keep them off the streets and like a festival of 500,000 people
09:45was a very beautiful turnout, you know?
09:47I hope we have more of them, you know?
09:49During the interview, the soft-spoken musician brought some renewed focus to his craft as a genuine guitar genius.
09:55He was open to giving some detailed answers about his approach to his instrument and anxiety.
09:59Before his untimely death in 1970, this was one of his more enlightening television interviews that Hendrix ever gave, and
10:06certainly an important one given its place in his career.
10:09You know, I like to, like, play to myself in, like, in the room or before we go on stage
10:14or something like this.
10:15Or whenever I feel, like, you know, whenever I feel down or depressed or whatever, you know?
10:18I just go on and play.
10:20Number 10.
10:21Prince Talks to Arsenio Hall.
10:23The Arsenio Hall Show.
10:24It wasn't every day that Prince gave an interview.
10:27Holding his cards close to his chest, the enigmatic figure preferred to speak through his music.
10:31And here's the interesting thing.
10:33Do you have a cell phone?
10:37No.
10:38See, I'm always shocked when I hear from you.
10:41But how do you survive in this world without a cell phone?
10:44Everybody I know has one.
10:45Even if he was in the later stage of his career, he still brought along his mischievous personality to Arsenio
10:50Hall's show.
10:51Hall also mentioned that the Purple One was the first person that contacted him after his show came back in
10:56the 2010s.
10:57The host also discussed his guest's opinions on everything, from technology to his pre-fame years.
11:03Along with interesting digressions about reality TV and mentorship, the artist teased the depth of his unreleased catalog.
11:10Audiences even got to see Prince showing off his sense of humor when Hall brings up the glory days.
11:14I remember one time we went down the way south of Wilshire to an after-hours spot and hung out
11:22and partied.
11:23That's something that we'll probably get...
11:29Number 9. Elvis' Post-Army Interview
11:32When this musician got drafted, some people worried about his future in the entertainment business.
11:38He served his time in the U.S. Army and was honorably discharged in 1960.
11:42It's pretty hard to describe, I'll tell you.
11:44It's hard to get used to, you know. I mean, I've been looking forward to it for two years.
11:48His return to the United States prompted major media attention, as everyone wondered what would happen to Elvis Presley.
11:54This post-war debriefing included a preview of what was to come.
11:57It was likely among the more hot-button interviews of its time for die-hard fans.
12:01There might have been some uncertainty about his career, but Presley seemed focused on getting right back into music and
12:07movies.
12:07The first thing I have to do is to cut some records.
12:11And then after that, I have the television show with Frank Sinatra.
12:19And then I have the picture with Mr. Wallace.
12:22His fourth album, Elvis' Back, officially reintroduced him to the general public.
12:27The rest was history, with some of his greatest successes ahead of him.
12:31Number 8. Madonna's Cigar Smoking Interview
12:34Late Show with David Letterman
12:35Sitting down for an interview on Late Night with David Letterman, Madonna seemed intent on entertaining the audience.
12:41The pop star smoked a cigar and talked openly about her career.
12:45You used to be really kind of, like, cool.
12:47I know. There is no bigger dweeb than me.
12:52Money's made you soft.
12:53Really? You think so?
12:54Yeah.
12:54In what sense?
12:55Because you just kiss up to everybody on your show now.
12:58Along with her candid answers, the vocalist didn't mind dropping a few swear words.
13:02But Letterman looked both flustered and amused by his guest's unreserved demeanor.
13:06Finding the woman at a peak cultural moment, this interview seemed like a far cry from the most PR-friendly
13:11junkets of today's world.
13:12There seems to be a lot of confusion right now.
13:14Yeah, guess why?
13:19Is it because I've been saying...
13:23The politically incorrect nature of this segment might shock you or prove to be refreshing from today's perspective.
13:29Number 7.
13:30Whitney Houston talks to Diane Sawyer.
13:32Primetime.
13:34Not all iconic interviews are fondly remembered.
13:36Others fall into a more complicated category, showing an artist on the brink of self-destruction.
13:41But that's not just thin.
13:44No, it isn't.
13:46Diane, tell me.
13:47Do you know?
13:48It's scary thin.
13:50Whitney Houston talked to Diane Sawyer about her weight, drug habits, and personal life in 2002.
13:56The singer didn't love the questions, but we couldn't blame her either.
13:59Sawyer asked Houston about some controversial subjects, and the answers became infamous in their own right.
14:05Quotes like crack is whack seemed to grab headlines, while others worried about the diva's overall health.
14:10First of all, let's get one thing straight.
14:12Crack is cheap.
14:14I'd make too much money to ever smoke crack.
14:17Let's get that straight, okay?
14:19We don't do crack.
14:21We don't do that.
14:22Crack is whack.
14:24It's yet another example of the inability for certain famous people to get the proper help they need.
14:29The interviewer's infamous Britney Spears interview also reveals the effects of toxic media coverage.
14:35Number 6.
14:36Kurt Cobain talks to MTV.
14:37MTV.
14:38As one of the most influential musicians of the early 1990s, Kurt Cobain was the subject of many interviews.
14:44His band Nirvana rose to the mainstream with the success of Nevermind.
14:48We wanted to put out a record that we would listen to at home.
14:53In the middle of the chaos, he sat down with MTV to put words to his career and personal life.
14:59Cobain offered up some sobering thoughts about his artistry.
15:01There were also some insights into his mental and physical health at the time, with indirect references to his complex
15:07headspace.
15:08He talked about the trouble with his stomach that plagued him through most of his fame.
15:11I was in pain, I mean, I was in pain for so long that I didn't care if I was
15:17in a band, I didn't care if I was alive.
15:20It's both heartbreaking and intriguing to watch him in this state, dealing with stardom with his trademark delivery.
15:26Number 5.
15:27Warren Zevon's Final Time on Letterman.
15:29Late Show with David Letterman.
15:31Near the end of his life, Warren Zevon returned to The David Letterman Show to talk with his old friend
15:36about mortality.
15:37To me, you look and seem remarkably healthy.
15:40I mean, that's kind of an odd...
15:42Well, don't be fooled.
15:44Don't be fooled by cosmetics.
15:47How do you feel?
15:48Well, I don't feel as bad as they say I am.
15:53He bravely described his own medical history, and his perspective on all things music and sandwiches.
15:59Letterman was open to having a tough conversation about terminal illness and regret.
16:03Before some moving musical performances, Zevon offered up what might be his most profound moment in pop culture.
16:09After all of the hit singles and funny lyrics, he was able to sit down with a late-night legend
16:14and talk about what really matters.
16:16You know, you put more value on every minute.
16:18You do, Liv.
16:20I mean, I always thought I kind of did that.
16:21I really always enjoyed myself, but...
16:23Yeah.
16:24But it's more valuable now.
16:26You're reminded to enjoy every sandwich and every minute of playing with the guys and being with the kids and
16:33everything.
16:33For anyone unfamiliar with this particular guest, this interview will be a great start to understand a complicated American songwriter.
16:41Number 4.
16:42Sex Pistols Shake Up Bill Grundy.
16:44Today.
16:45When it comes to this punk band, all bets are off.
16:48The Sex Pistols shook up the music industry in the late 1970s with their aggressive riffs and political lyrics.
16:54I want to know one thing.
16:56What?
16:57Are you serious?
16:57Are you just trying to make me laugh?
16:59On this particular talk show, they also showcased their public persona as troublemakers.
17:04Each of the members seemed eager to let Bill Grundy have it, including the outspoken frontman Johnny Rotten.
17:10While the host attempted to maintain order, he was unable to close the floodgates.
17:14This might have been the essential interview to encapsulate the band's place in pop culture.
17:18It's also a nice metaphor for the punk movement washing over the mainstream, sending the establishment running for the hills.
17:24Well, that's it for tonight.
17:26The other rocker, Abel, and I'm saying nothing else about him, will be back tomorrow.
17:30I'll be seeing you soon.
17:31I hope I'm not seeing you again.
17:33Number 3.
17:34David Bowie Criticizes MTV
17:36MTV
17:37Spending much of the 1970s exploring genres and different personas, David Bowie entered the 1980s as a pop crooner, looking
17:44to conquer another generation.
17:46I'm just floored by the fact that there's so few black artists featured on it.
17:50Why is that?
17:51I think that we're trying to move in that direction.
17:54We want to play artists that seem to be doing music that fits into what we want to play for
17:59MTV.
18:00MTV's Mark Goodman interviewed him and received notable pushback in this intriguing clip.
18:05The singer offered up a pointed critique of the network and their alleged focus on white artists over black artists.
18:11While the interviewer attempted to defend his employer, Bowie kept digging to understand what he saw as an obvious injustice.
18:17Do you not find that it's a frightening predicament to be in?
18:20Yeah, but less so here than in radio.
18:23Even though he likely received attention and renewed fame thanks to MTV, Bowie wasn't above speaking his mind.
18:29Number 2.
18:30Oprah Interviews Michael Jackson
18:32Michael Jackson talks to Oprah.
18:35Inviting viewers to his Neverland ranch, Michael Jackson joined Oprah Winfrey for a widely seen interview in 1993.
18:42The TV special came not long before a wave of allegations about the artist's personal life.
18:46When I was little, it was always work, work, work.
18:48From one concert to the next.
18:50If it wasn't concert, it was the recording studio.
18:53If it wasn't that, it was TV shows or interviews or picture sessions.
18:56It was always something to do.
18:59Winfrey seemed intent on breaking down the pop facade created on albums like Thriller and Bad.
19:05The interviewer didn't turn this into an interrogation, but she did try to explore Jackson's life from childhood to international
19:11superstar.
19:12This included some harsher questions about the performer's health and image.
19:16You know, let's just put it this way.
19:18If all the people in Hollywood who have had plastic surgery, if they went on vacation, there wouldn't be a
19:24person left in town.
19:27I think you might be right.
19:28The singer cleared the air on some lingering rumors, but he also gave the viewers a lesson in moonwalking.
19:36Are you a musician, singer, producer, or band?
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19:46Earn $1,000 per song or $500 plus a 50% revenue share.
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20:02Number 1. John Lennon and Yoko Ono have a bed-in.
20:06These artists became politically conscious during a volatile time.
20:09John Lennon and Yoko Ono staged two events called bed-ins, featuring interviews and talks from various public figures.
20:15All we're saying is if you think you can do better, do it.
20:18You top it. Stop asking us, do you think it's going to work?
20:21You know, do something yourself.
20:22These unique events in Amsterdam and Montreal were a noteworthy change for Lennon's public image.
20:28During the sessions, some skeptics asked the two about their activism.
20:31Hoping for a positive outcome, the mixed reception led to another notable chapter in the man's historic career.
20:37It captured him at a pivotal point as the Beatles approached a breakup,
20:41with a separation inspiring fun interviews from the other members.
20:44Yoko sat in that very chair.
20:52Well, I bet many people have sat in this chair.
20:55Well, a lot of people have sat in it, but I was just thinking...
20:56I saw the show, it was very nice.
20:58Priming his own solo aspirations.
21:00This came near the time of Plastic Ono Band, and singles like Give Peace a Chance.
21:05Do we forget another insightful interview from music history?
21:08Let us know in the comments below.
21:09Let us know in the comments below.