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Making Heads Or 'Tails' Of Success: Lisa Loeb Celebrates 25 Years Of Her Major-Label Debut Album

Lisa Loeb in 1994

Photo by Gary Gershoff/Getty Images

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Making Heads Or 'Tails' Of Success: Lisa Loeb Celebrates 25 Years Of Her Major-Label Debut Album

GRAMMY.com talks to Loeb about making 'Tails' amidst the meteoric rise of "Stay," navigating "acoustic guitar equals folk music" pigeon-holing, and releasing her most recent album, 'A Simple Trick to Happiness'

GRAMMYs/Sep 23, 2020 - 07:28 pm

"We have an audience for a song," singer-songwriter Lisa Loeb told Entertainment Weekly in the fall of 1995, "I hope they want to hear a whole album."

As the first unsigned artist to hit No. 1 on the Billboard Hot 100, Loeb was situated within the unique position of having to balance the television-and-radio promotional whirlwind around her platinum-selling single "Stay (I Missed You)" from the Reality Bites soundtrack, while also recording her major-label debut album for her recent signing to Geffen Records. From indie rock bandleader and solo acoustic troubadour to labelmates with pop culture juggernauts like Nirvana, Aerosmith, Guns N’ Roses, Hole and Weezer, all eyes were on Loeb to see how she would follow up her massively successful, charting-topping single.

The charmingly up-to-the-task result was Tails—her first of two back-to-back Gold-selling albums—which celebrates its 25th anniversary this month. Loeb will be commemorating the event on Saturday, September 26, with her "One Night Only World Tour"—a special two-show live streaming event where she will perform the entire album acoustically for the first time in her career.

To help mark the two-and-a-half-decade milestone, GRAMMY.com recently hopped on the phone with Loeb to discuss making her Tails album amidst the meteoric rise of "Stay," navigating "acoustic guitar equals folk music" pigeon-holing, and releasing her most recent album, A Simple Trick to Happiness.

Lisa Loeb: Since Tails was my first major-label album, like a lot of artists in that position, it was an assembly of songs that I had written over the previous few years that I now wanted to share with a larger audience. Some of the songs I was most excited about re-recording or working into a fuller band context had already appeared on other recordings I had made. That was not just the case with Tails, but also with my next album, Firecracker. When I was making records back in college, I knew it was time to make a new album every time I had a collection of 12 to 14 new songs. So, the biggest focus of that time period was just buckling down and recording them for my new album. Working with Juan Patiño, my co-producer, we had already done a lot of demo recording of these songs before "Stay" had even come out.

Even without an album release, the expansive mainstream success of "Stay" required Loeb to maintain a busy datebook of appearances—The Late Show with David Letterman, the MTV Beach House, picking up International Breakthrough Act from Tom Jones at the 1995 Brit Awards—throughout the latter half of ‘94 and well into the summer of ’95. All the while, Loeb and Patiño were spending as much time as they could recording and re-recording the songs that would comprise the Tails album.

Lisa Loeb: During that period, it was important for me to promote "Stay" and do some touring and appearances around that, but to also make sure we were recording the best versions of the songs for my new album. Juan and I tended to go deep into the production side of things. We’re both perfectionists, or in a kinder way, I’ll say that we were quality-control freaks. I’ve heard us compared to people like Don Henley and Fleetwood Mac, where production is very labor intensive and detail-oriented. We wanted it to feel easy and natural, but we also had very specific ideas of what it should sound like. We were very intense about the whole process. Plus, since it was my first major-label album, we bought into all the stories of our favorite bands and felt like it was such a big deal. I wanted to maintain my grassroots following that I had built but having a major-label deal meant a lot and we were very reverent to that idea. We wanted to live up to that "major-label debut" hype. 

That "major-label debut" hype came courtesy of Loeb signing to Geffen Records, the victors of a multi-label bidding war centered around the up-and-coming star. However, instead of all of the attention being paid to just her recent hit, it was one industry vet’s connection to her early material that was one of the major contributing factors to her decision to finally sign with Geffen.

Lisa Loeb: Geffen had an A&R person named Jim Barber and he had shown interest in my music for years—way before we actually signed with them. It was a combination of his interest in me before I had a No.1 single and the fact that I thought Geffen Records was super cool for their intentional mixture of pop and indie music. I felt like I was somewhere in the middle of that: I was definitely an indie musician and leaned towards that genre, but I also had this one song that had become very popular. So sometimes I was treated like a pop artist, which, back then, there was more of a divide between indie and pop than there is today. I also liked David Geffen as an entrepreneur and his feel for making a major label feel like a boutique label.

As the finishing touches were being put on Tails for a late September ’95 street date, Loeb released "Do You Sleep?" as the album’s lead single. The song quickly became a Top 20 Billboard hit and Loeb performed it (alongside "Stay") on a Chevy Chase-hosted episode of Saturday Night Live less than two weeks after Tails was released. For the song’s music video, Loeb relied on her focused creative vision to collaborate with GRAMMY-winning director Sophie Muller (No Doubt, Garbage, Beyoncé).  

Lisa Loeb: Sophie had worked a lot with Annie Lennox and she had just done Hole’s "Miss World" video. There was always something very sparkly in her videos. My sister and I worked with Sophie and came up with a concept that was originally a little more abstract than the finished product turned out to be. I was working with a designer so that I could get my clothes exactly the way I pictured them, so I was completely involved in making and wearing the clothes I wore in that video. When we got to editing, the initial version wasn’t edited on the beat, and it was confusing to my brain. So, Juan and I went back in and re-edited it. In retrospect, I wish I could’ve let go more and just let Sophie direct because she does a really great job. It’s just once I get an idea in my head, I have to see it all the way through. Again, I should’ve just left it. I’m sure it was very beautiful.

Lisa Loeb visits "Saturday Night Live" in Fall of 1995
Photo by: Al Levine/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images

Loeb followed up the success of "Do You Sleep?" with the more raucous, electric guitar-fronted "Taffy"—an intentional artistic statement meant to keep the flawed "folk artist" characterizations at bay. With her first two music videos being completely devoid of her band and only fleeting images of an acoustic guitar making it into the final cut of "Do You Sleep?," Loeb was adamant that her band and her electric guitar would both get prominent placement in the "Taffy" music video. She carried this through on the late-night TV promo run for "Taffy" as well, cranking up a fuzzed-out vintage Gibson Les Paul Junior for her appearances on The Tonight Show with Jay Leno and Late Night with Conan O’Brien in early 1996.    

Lisa Loeb: I didn’t want to be too reactive after the success of "Stay," but I also didn’t just want to be pushed into the "acoustic" corner. I didn’t want to be seen as a folk artist at all. My music sounded like a band and I felt like the lead singer of my band; just like some of my favorite male music artists like David Bowie or Elvis Costello. However, during that period, if a female artist went by just her name, most people assumed you were a folk artist. That’s why I wanted to make sure my band name was included on everything and why I wanted to be seen and heard playing guitar. I realized early on that if you want people to know something about you, you have to show them.  

While Tails was largely considered a commercial and critical success, Loeb still occasionally experienced the seemingly inescapable (especially for artists who are female) cliché of comparison in some reviews of her album. One critic referred to her hit single "Do You Sleep?" as "a polite version of Alanis Morissette’s ‘You Oughta Know'" and another mused that "perhaps America is in search of a female Hootie." When asked about these sentiments 25 years later, Loeb charmingly takes it all in silver-lined stride.

Lisa Loeb: During that time, there seemed to be a lot of comparisons between me and artists like Alanis Morissette and Liz Phair. A handful of the female singer-songwriters at the time were being very direct in their songwriting, which was a great, strong viewpoint that wasn’t always there before with other female songwriters. I felt like my strong point was trying to write about situations from multiple angles. I wasn’t trying to be polite, just cerebral and communicative. Still neurotic, but in a craftier way. As far as Hootie, those guys are so nice and I feel like I might have played golf with them once at some VH1 thing. The thing I like about that comparison is that Hootie was very popular; people really loved their music and bought a lot of it.

I just feel like my music, with the exception of maybe something like "I Do" later on, was such a different thing. I always put a lot of thought and energy into having variety in my songwriting, arrangements and instrumentation. I try to steer clear of formulaic pop songwriting. I think it’s just the blessing-curse of being on the radio. I wasn’t such an indie rocker that I was angry about being on the radio—I was very happy to be on the radio—but I was aware that there could be a backlash once you’ve been on pop radio. On the other hand, it’s great problem to have for millions of people to have heard your music. It can just be kind of weird to be pegged for something that doesn’t accurately describe you.

In the 25 years since Tails was released, many of the album’s tracks can still be found in Loeb’s present-day setlists and in her audience’s shouted-out requests. But although the songs themselves have remained active in her ever-expanding repertoire, the specific recordings on her major-label debut are still moment-in-time snapshots capturing an incredibly important career milestone in the early days of her prolific and ongoing career.

Lisa Loeb: When I listen back to Tails, I still feel connected to that same "me" from 25 years ago. I hear somebody who is trying to do her best. I had taken so many voice lessons to better understand how to sing the songs I had written and I was so connected to them during the recording process. I also hear a lot of confidence and hope at the same time. There’s a bit of that freshman attitude of trying your hardest and not being afraid of letting that show; which should always be there. I’m still invested in every song, every performance, every video, every choice in the artwork. It meant a lot back then because I cared about it so much and I still do. Even now, I still make records the same way, just a little quicker.

After her first big steps into the mainstream with "Stay" and Tails, Loeb has maintained an impressively consistent pop culture profile with more Top 20 hits ("I Do"), more soundtrack appearances (“All Day” from The Rugrats Movie), her own reality show (#1 Single), a flurry of television appearances ("The Nanny," "Gossip Girl," "Community," "Fuller House"), animated voice-overs (Spider-Man: The New Animated Series, Special Agent Oso), film work (House on Haunted Hill, Fright Night, Hot Tub Time Machine 2), and more. However, her top priority remains writing songs, performing concerts, and recording albums. This trio of activities has expanded to include children’s music in recent years, including her celebrated 2016 album Feel What U Feel, which won a GRAMMY for Best Children’s Album. Continually blending and balancing both (often overlapping) audiences, Loeb released her newest "grownup" album, A Simple Trick to Happiness, earlier this year.  

Lisa Loeb: With A Simple Trick to Happiness, I’ve been able to co-write and collaborate in ways that allowed me to come up with something very personal and the songs have proven themselves to connect me to others. People really seem to relate to these songs and they seem to provide people with a lot of comfort. Like with the music video we did for "This Is My Life," it captures the craftiness and thoughtfulness that we have to have each day to puzzle our lives together. We’re so careful and we’re working so hard, but everything might change in the blink of an eye, and then we have to be right back at it again. If you look at the whole album, there’s an understanding that life can be difficult but also that there is a way to reframe things.

As a songwriter, I didn’t want to be one of those grown-ups who didn’t know what to write about once they weren’t writing about love and heartbreak as a twenty-something. I’ve always strived to tap into what I’m going through in the present moments. Honestly, making A Simple Trick to Happiness still felt a little like it did when I made Tails 25 years ago: It’s a new record, I want people to hear it, and I feel like the songs might really mean something to people.

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The Magic Of ESSENCE 25th Anniversary Celebration: "It's Like A Family Reunion Even Though You Don't Know Everybody Here"

Mary J. Blige

Photo: Erika Goldring/Getty Images

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The Magic Of ESSENCE 25th Anniversary Celebration: "It's Like A Family Reunion Even Though You Don't Know Everybody Here"

"Being able to celebrate black culture at this magnitude means everything because we've never had anything like this," MC Lyte said

GRAMMYs/Jul 9, 2019 - 04:57 am

New Orleans' Central Business District looked starkly different Monday morning as city locals hurried to work in ties and business attire. Gone were the crowds of people walking around in the heat of the southern city in their most fabulous summer outfits as R&B, hip-hop, soul and more took over the Big Easy's Superdome once again for ESSENCE Fest 25th anniversary

This year locals and those from far and wide came together to watch performances from iconic artists like Missy Elliott and Mary J. Blige and hitmakers like Pharrell Williams and Timbaland to emerging artists like Normani and H.E.R at the biggest festival celebration of black culture in the country that took place July 5–7. But the festival was more than just music, it was a space where conversations around food, politics, business and more.  

While the fest has happened in New Orleans since its inception, this year was different for great reason. The fest, born out of ESSENCE magazine aimed mostly to its black female readership, celebrated 25 years of brining different parts of black culture under one roof and the musical artists performing reflected on the milestone. MC Lyte, who curated one of the ESSENCE events that took over the venues all over the city, with women in hip-hop broke down why the fest means so much. 

"Being able to celebrate black culture at this magnitude means everything because we've never had anything like this. Growing up, we certainly didn;t at least in my era and even now to date. The ESSENCE Music Festival is truly one of a kind," she said. 

For some performers like New Orleans native  PJ Morton, the 25th anniversary was a very special moment as it brought him back full-circle.  

"I've been going to this festival since I was 14 years old and really changed my life as far as wanting to be a musician and seeing how it was presented, " he said. "When ESSENCE asked me to be a part [of the festival] again, I said 'I just don't want to play it again, I've played it before, let's do something special. Especially to kind of commemorate all these things, winning the GRAMMY award this year and me being able to come home. Part of winning that GRAMMY and writing those songs and making that album was me leaving L.A. and moving back home to new Orleans three years ago, so for me it was just a perfect full-circle moment to do a recording."

The singer made history during the night of his performance by recording a live album at the fest for the first time ever.

But he wasn't the only local with special ties to the fest. Rising star Normani, also a big easy native and first time performer at the fest, shared why the fest is so special to her.

"I'm grateful that I can finally be a part of it. For as long as I can remember growing up ESSENCE was ESSENCE and it's just really coolfor me to be a prt of it. My grandmother, she came, my nanny came,  my uncles they came out too and it's beautiful for me to be able to really represent my city in such a way, she said."

The opportunity to talk and have conversations with other women in particular is what excites singer Mumu Fresh the most about the festival. "[Women] who are affirming you and just sharing their stories."

"It's like a family reunion even though you don't know everybody here.They've shared your experience and everyone's just loving and gorgeous, all day long I've been walking by strangers who have been like 'YES hair, YES shoes YES face' and I'm like 'Awww heeyy, you too.' It's really fun, it's really beautiful."

NAO Talks Vulnerability & Being Black And British At ESSENCE Fest

Quarantine Diaries: Teenear Is Reading, Doing Cardio & Making Acai Bowls

Teenear

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Quarantine Diaries: Teenear Is Reading, Doing Cardio & Making Acai Bowls

As the coronavirus/COVID-19 pandemic continues to rock the music industry, GRAMMY.com reached out to a few musicians to see how they were spending their days indoors

GRAMMYs/Aug 19, 2020 - 08:10 pm

As the coronavirus/COVID-19 pandemic continues to rock the music industry, GRAMMY.com reached out to a few musicians to see how they were spending their days indoors. Today, Miami-based pop/R&B upstart Teenear shares her Quarantine Diary. Teenear's latest single "Free" is available to hear now.

[6:30 a.m.] First thing that I do when I wake up is brush my teeth so I can get to the gym on time without my trainer yelling at me! 


[9:00 a.m.] As soon as I get back home, I hop on the treadmill to get my cardio out of the way. I've really been trying to make sure I stay active during this time of having to be stuck in the house! 

 
[12:00 p.m.] By this time, I'm hopping out of the shower, my adrenaline has finally gone down, and I'm able to make myself and Acai bowl and write in my journal. I also take this time to hit up my team and figure out what I have to get done for the day. 
 
[2:00 p.m.] I start reading the books that I read daily. One of the books I started reading recently is The 365 Bible, which gives you specific versus on each day, and it reads in chronological order of how all the stories actually went. Another book I’m into is The Purpose Driven Life by Rick Warren. This is one amazing book and I’m so happy my mom blessed me with this read! The last book I’m reading right now is A Singer's Compass that is actually written by my vocal coach Cassandra Claude. 

 
[4:00 p.m.] I’m getting dressed to go outside and shoot some content. Creating content from home has definitely become a huge daily task but I'm grateful for it because now I’m able to find new ways to be creative and showcase my personality to my fans.

 
[7:00 p.m.] I try to take this time meditate. Throughout this whole pandemic I’ve been trying to get into new things and meditation has played a big role in me figuring out a little bit more about myself and my surroundings. No, I’m not a yoga person yet! I have tried countless classes and it's not for me just yet, but one day I’ll get into it! 

 
[9:00 p.m.] Usually around this time, if I’m not sitting in a corner somewhere in the house singing, I’m most likely in my bathroom trying a new beauty product I just ordered online. The ads have gotten a little too good during this quarantine!

If you wish to support our efforts to assist music professionals in need, learn more about the Recording Academy's and MusiCares COVID-19 Relief Fund.

If you are a member of the music industry in need of assistance, visit the MusiCares website.

2018 GRAMMYs: Body Count, India.Arie To Perform At Premiere Ceremony

India.Arie

Photo: Dia Dipasupil/Getty Images

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2018 GRAMMYs: Body Count, India.Arie To Perform At Premiere Ceremony

Hosted by Paul Shaffer, the annual ceremony will also feature performances by Jazzmeia Horn, Taj Mahal, Keb' Mo', and Stile Antico

GRAMMYs/Jan 18, 2018 - 08:30 pm

Each year, the GRAMMY Awards Premiere Ceremony kicks off Music's Biggest Night by recognizing GRAMMY winners in more than 70 categories, complete with outstanding performances. We now have all the exciting details on the 2018 installment of the annual event.

This year's Premiere Ceremony will take place at The Theater at Madison Square Garden on Sunday, Jan. 28, preceding the 60th GRAMMY Awards telecast. Singer, composer and instrumentalist Paul Shaffer will host the ceremony and will serve as musical director while his World's Most Dangerous Band will serve as the house band.

Current GRAMMY nominees Body Count, India.Arie, Jazzmeia Horn, Taj Mahal and Keb' Mo', and Stile Antico will perform, while current GRAMMY nominees Zac Brown, Natalie Grant and Bernie Herms, Ledisi, Lisa Loeb, Neil deGrasse Tyson, and former Recording Academy Chair Jimmy Jam will serve as presenters.

The Premiere Ceremony will be streamed live internationally via GRAMMY.com from 3–6 p.m. ET and will be available on demand following the broadcast.

Hosted by James Corden, the 60th GRAMMY Awards will be broadcast live on Sunday, Jan. 28 on CBS from 7:30–11 p.m. ET/4:30–8 p.m. PT.

King Bach On His Comedy Album 'Medicine,' Loving Ludacris & Trying Not To Throw Up

King Bach

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King Bach On His Comedy Album 'Medicine,' Loving Ludacris & Trying Not To Throw Up

The YouTube and former Vine star opens up to the Recording Academy about creating his first comedy album, who he listened to growing up and why laughter has been a cure-all in his life

GRAMMYs/Oct 4, 2019 - 11:54 pm

Andrew Bachelor, otherwise known as rising comedy titan King Bach, is definitely on his way to achieving royalty. 

Starting out producing comedy sketches on YouTube, Bachelor eventually switched to the now-defunct short-form outpost Vine, where he'd go on to amass more than 15 million subscribers and more than five billion views. Nowadays, the funnyman is dipping his toes into the TV and music world, where he currently stars in IFC's variety sketch series "Sherman's Showcase," among other things.

Meanwhile, Medicine, which dropped in mid-August, is his debut comedy album, and is filled with 15 true-to-life tracks—with music videos—that skewer everything from his weak stomach ("Bulimic") to the lies people tell each other when they first meet ("Secrets"). 

Below, Bachelor opens up to the Recording Academy about why laughter is truly the best Medicine, who he listened to growing up and the different ways he utilizes social-media platforms to reach new audiences. 

What sparked the idea to make a comedy album?

I've always loved music, ever since I was younger. And when I started making the comedy skits, I actually thought of making a parody music video, and I just love putting together music that people just like to listen to and have fun with listening to it and having a laugh at the same time.

So I figured why not make original music that I own and, I could just share with everyone and not feel any type of way of me taking someone else's style. This is my style, my unique style. So yeah and then I figured it's a comedy album and they're saying laughter is the best medicine, so I named the album Medicine, because every track they're laughing at.

Who did you listen to growing up?

I listen to a lot of Ludacris, Ludacris is my favorite rapper since I was little. Just his style, his energy, I like songs that have a lot of energy behind them. Now music has changed though we realize, that energy has kind of tapered down a little bit. So most artists, it's a lot of mumbling going on, it's more like vibes and feeling it out as opposed to the lyrics. So I'm doing a mixture of both.

Yeah, we've been hearing a lot of "genre labels don't matter anymore" nowadays.

Yeah the whole thing is, what I realized in doing comedies, why it's so good, when you're laughing about a joke or anything, you forget all your problems. You forget about the bad day you had, you forget about your breakup, you forget about somebody who's passing. You just forget about everything and you're literally focused on that joke that that made you laugh in that moment. So that's the mood that I want people to feel like when they listen to the album, they can just forget about everything else and just enjoy the music and just stay present.

Have you personally used comedy as a coping mechanism?

Yeah, with everything, it kind of puts me in a better mood and lets me forget. The way I look at is, I'm being myself, I am being unique. Some people may find it funny but I'm being me, like these are my point of views. Every song on the album is a situation that happened in my life. So it's a situation that happened in my life and I took it and I found the comedy in it.

There's a song on there called "Bulimic." I have a very weak stomach and throughout the days I'm constantly trying to stop myself from throwing up. And it's just been something I've dealt with since I've been seven years old. So I tried to find the light of that and I made a song called "what you going to do if I throw up on you?"

Are any other themes that have come up repeatedly in your comedy that you've touched on with Medicine?

Yeah, there's a song on there called "Secrets," and it's about everyone letting out the secrets and being honest. And the way I directed in film, that music video was pretty much like a YouTube skit. The concept of the video was the speed dating situation, and everyone thinks that speed dating is going regular, but then the speed dating announcer, he announces that she puts truth serum in the guys drink. And it forces them to let out their deepest and darkest secrets. So these guys are confessing their secrets against their will. So that's how I kind of shoot my skits as well, I come up with a concept and I just shoot it around that.

You became pretty famous from using Vine, which sadly doesn’t exist any longer. Have you embraced the similar-minded Tik Tok to create the same short-form comedy? 

Yeah, listen, I'm a creator at the end of the day and I am on the social media application. So I'm on Tik Tok, I'm on Facebook, Twitter, Instagram, I'm on everything. And I'll just take one video and I'll just post it everywhere. So if someone only has Tik Tok, they're getting it on Tik Tok. If they only have Facebook, they're getting on Facebook, so I use them all. You name the app, I got it.

So what's your strategy when deciding how to best utilize different apps?

I kind of see how the platform is being used and I kind of adapt to that. So Tik Tok is more music-based, so if I have an idea and it's music based and it's a fun, bubbly, energetic vibe that'll go on Tik Tok. So yeah definitely got to think about, it's like you got to know your audience.

Bob Marley's London Home Honored With English Heritage Blue Plaque