Best Album Covers of All Time

Summary

Podcast Summary: All Of It – "Best Album Covers of All Time"

Episode Details:

• Title: Best Album Covers of All Time
• Host: Alison Stewart
• Guest: Joe Lynch, Executive Digital Editor at Billboard
• Release Date: June 23, 2025
• Duration: Approximately 21 minutes

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1. Introduction to Album Art (01:15 - 03:17)

Alison Stewart opens the episode by highlighting the integral relationship between music and its visual representation. She emphasizes that while music is primarily an auditory experience, album covers play a crucial role in shaping a band's identity and influencing consumer engagement.

Alison Stewart: "A good album cover is as evocative of a band as their music is."

She references iconic album covers such as Abbey Road, Dark Side of the Moon, and Nevermind, setting the stage for a deeper exploration of album art's significance.

2. The Origin of Album Covers (02:07 - 03:19)

Joe Lynch delves into the history of album covers, tracing back to their inception in 1939 by Alex Steinweiss. Steinweiss, a young graphic designer from Brooklyn, introduced the concept while working at Columbia Records. His innovative idea was to attract more buyers by creating visually appealing album covers, transforming the way music was marketed and consumed.

Joe Lynch: "Steinweiss... pitched the idea that there's this new thing we're doing. It's probably going to sell more copies if there's stuff on the front that catches someone's attention."

3. Introduction of the Best Album Cover Category in the Grammys (03:57 - 05:37)

Alison announces the addition of the Best Album Cover category to the Grammy Awards starting in 2026. She discusses with Joe the implications of this new category, noting that while the Grammys have previously had awards related to album packaging and design, this focused category aims to honor the art of album covers specifically.

Joe Lynch: "The decision to focus just on album cover... the first thing that hits you about a record that kind of decides, am I going to click play, Am I going to buy this?"

He reflects on the historical context, mentioning that the first Grammy Award for album cover was given to Frank Sinatra in 1959 but was later merged into broader categories like Best Recording Package.

4. Impact of the Streaming Era on Album Art (05:37 - 07:14)

The conversation shifts to how the transition from physical albums to digital streaming has transformed album cover design. Joe explains that smaller digital formats necessitate simpler and more striking designs to capture attention on screens.

Joe Lynch: "A lot of artists pivoted to these really simple, distinct designs... designed to be imitated, designed that you were going to put that out and then someone was going to take [their] name out and put their own name in that font or put little meme jokes in the [album] font and share that on social media."

He cites examples like Beyoncé's self-titled album and Drake's minimalist covers, highlighting their effectiveness in the digital landscape.

5. Social Media's Influence on Album Covers (07:14 - 08:31)

Listeners contribute their thoughts on the influence of social media on album art. A particular discussion revolves around Sabrina Carpenter's controversial album cover, exploring themes of self-expression versus sexualization.

Listener: "Is she a woman in control of her image or is she being sexualized?"

Joe acknowledges that social media has made album covers a platform for discourse, sometimes intentionally provoking debate to increase visibility and engagement.

Joe Lynch: "I think social media has changed it. But... if you really whiff it, you might get blowback."

6. Listener Calls: Sharing Favorite Album Covers (08:31 - 20:58)

Alison invites listeners to share their favorite album covers, leading to a series of contributions that highlight diverse tastes and eras. Highlights include:

• Donna from Mount Vernon appreciates Abdullah Ibrahim's Water from an Ancient Well for its evocative jazz imagery and **Cat Stevens' T for its nostalgic significance.

  Donna: "There's a flow of water, there's some blue. I just love it."

• Gabriel from Brunswick, Georgia discusses The Rolling Stones' Sticky Fingers designed by Andy Warhol, noting its interactive zipper feature and the resulting practical issues with vinyl shipping.

  Gabriel: "It's a photograph of a pair of jeans... but it's fun. You pull down the zipper and there's underwear behind it."

• Jeff from the East Village highlights Roxy Music's Country Life for its controversial yet iconic imagery of semi-clad women, which sparked significant debate upon release.

  Jeff: "That got so much controversy that they even released it in a green opaque plastic sleeve for a while."

• Additional contributions mention Jethro Tull's Stand Up and Wu-Tang Clan's ODB, showcasing the variety in album art appreciation.

7. Emerging Trends and the Role of AI in Album Cover Design (11:49 - 13:53)

Discussions turn to the evolving landscape of album art in the age of artificial intelligence. Joe comments on the mixed reactions to AI-generated art, noting skepticism among traditional artists and designers.

Joe Lynch: "People are like, you know, that's it. The human element is out. It doesn't count anymore. This isn't real art."

He speculates that while AI will become more accepted over time, its current use in high-profile album covers may provoke controversy and backlash.

8. Billboard’s 100 Best Album Covers of All Time (13:53 - 20:58)

Alison and Joe delve into Joe Lynch's curated list of the 100 Best Album Covers of All Time. Joe explains his criteria, emphasizing iconic imagery, cultural transcendence, and the ability to push artistic boundaries.

Joe Lynch: "The criteria was to think of a combination of undeniably iconic images that kind of transcend the album... did it push the art form forward as album art?"

Highlights from the List:

• Number 10: The Notorious B.I.G.'s Ready to Die (1994)
  Celebrated for its juxtaposition of innocence and grit, featuring a baby-like image symbolizing the harsh realities Biggie often rapped about.

  Joe Lynch: "It's a baby with an Afro sitting there on an all white background... the gritty realism that, you know, Biggie was all about."

• Number 1: The Velvet Underground & Nico's The Velvet Underground & Nico
  Recognized for Andy Warhol's iconic banana design, which includes an interactive element where the banana can be peeled to reveal another image.

  Joe Lynch: "Andy Warhol and Lou Reed both loved a phallic symbol, I got to say."

• Cyndi Lauper's She's So Unusual
  Joe cites this cover for its vibrant colors and Annie Leibovitz's photography, capturing Lauper's unique style and the pop explosion of the era.

  Joe Lynch: "It's a beautiful explosion of color... frames it so perfectly. It's like everything in the frame... it's a Stanley Kubrick movie or something."

9. Conclusion and Final Thoughts (20:58 - End)

Alison wraps up the discussion by thanking Joe Lynch for his insightful contributions and highlighting the enduring importance of album art in the music industry. She encourages listeners to continue sharing their favorite album covers and engaging with the cultural narratives they represent.

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Notable Quotes with Timestamps:

• Alison Stewart (01:15): "A good album cover is as evocative of a band as their music is."

• Joe Lynch (03:17): "Steinweiss... pitched the idea that... there's stuff on the front that catches someone's attention."

• Joe Lynch (03:57): "The decision to focus just on album cover... the first thing that hits you about a record that kind of decides, am I going to click play."

• Joe Lynch (05:37): "Designed to be imitated... designed that you were going to put that out and then someone was going to take [their] name out and put their own."

• Joe Lynch (07:43): "I think social media has changed it... you might be getting blowback."

• Donna from Mount Vernon (09:26): "There's a flow of water, there's some blue. I just love it."

• Gabriel from Brunswick, Georgia (10:16): "It's a photograph of a pair of jeans... but it's fun."

• Joe Lynch (13:53): "The criteria was to think of a combination of undeniably iconic images that kind of transcend the album."

• Joe Lynch (15:35): "Ready to Die... it's this baby with an Afro sitting there on an all white background."

• Joe Lynch (19:35): "It's a beautiful explosion of color... it's like everything in the frame... it's a Stanley Kubrick movie."

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This episode of All Of It offers an engaging exploration of album cover art, its historical roots, evolving trends in the digital age, and the cultural conversations it continues to inspire. Through expert insights and listener interactions, Alison Stewart and Joe Lynch provide a comprehensive understanding of why album covers remain a vital aspect of musical expression and consumer experience.

Transcript

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[Alison Stewart]

This is all of it on wnyc. I'm Alison Stewart. Music may be an auditory experience, but before you drop the needle on the record or click Play on your phone, you're probably already interacting with it through art. A good album cover is as evocative of a band as their music is. Just visualize four men, one barefoot, walking across the street on a crossing, or a light going through a prism and coming out a rainbow, or a naked baby swimming towards a dollar bill dangling from a fish hook. You probably know that I've already talked about the album covers for Abbey Road, Dark side of the Moon, and Nevermind. Now, the 2026 Grammys are adding a new category to this to the awards this week. It's called Best Album Cover. Joining us now to discuss this and take us through a list of his favorites is Joe Lynch. He's the executive digital editor at Billbird. Hey, Joe.

[Joe Lynch]

Hi.

[Alison Stewart]

So album art was first introduced to us as a concept in 1939 by Alex Steinweiss.

[Joe Lynch]

Steinweiss, yes.

[Alison Stewart]

Who is Alex Steinweiss?

[Joe Lynch]

Alex he was, I believe he was 22 or 23 at the time. So he was just a kid from Brooklyn who went to Parsons, was working at Columbia Records as someone's assistant, and he kind of pitched the idea like, hey, we might sell more copies of this. You know, these albums, which were at the time a new concept, you know, they really only started putting 78s, which were the precursor to 45s, together in these albums, which were called that because they resembled photography albums, you would like flip the COVID open and, and there'd be 178 and you flip it over and another one. So it was literally an album collection of singles. Anyways, he had the idea that there's this new thing we're doing. It's probably going to sell more copies if there's stuff on the front that catches someone's attention. So he used his graphic design, know how, combined some elements, graphic elements and a photograph, and did Rogers and Hart's smash hits, which of course the duo that did Ladies of Tramp and, you know, My Funny Valentine and all those goodies.

[Listener]

So that's where it started.

[Joe Lynch]

That's where it all started.

[Alison Stewart]

1939 listeners, we want to hear from you. What's your favorite album cover? Call or Text us at 2124-3396-9221-2433 WNYC. Tell us why album cover art is important to you. What do you think makes an album cover really iconic? Give us a call. 212-433-9692. Or maybe you're a graphic designer who's worked on album covers. We want to hear about it. 212-433-969. What did you think when you heard that the Grammy Awards were going to add Best Album Cover category?

[Joe Lynch]

I thought it was really exciting. And I did that thing where I was like, wait, don't they kind of have something like that already? Which they do. They have best recording package, which is kind of the whole deal that'll include your album artwork, your liner notes, if you have a fancy box set that has reproductions of tickets or whatever, that'll also be in it. So the decision to focus just on album cover I thought was fascinating and worthwhile because it's, as you mentioned earlier, it's the first thing that hits you about a record that kind of decides, am I going to click play, Am I going to buy this? Whatever. But it isn't new, as my co worker Paul Grein told me. Actually the first Grammy Awards, 1959, there was best album cover given to Frank Sinatra. He kind of did the art design on one of his records. But pretty quickly the academy struggled to figure out how to do it. They switched it between classical album covers and pop album covers. And then they once again decided, that's not quite working. Let's give an award for photography on album covers and then separate ones for graphic design. And they just kind of muddled with it over the years and it eventually evolved into best recording package, which still exists. That's what we still have. And then for whatever reason, they decided, let's also give love to the album covers. I would guess they've brought in so many new members recently. You know, perhaps there's a lot of artists, a lot of folks who are thinking, you know, recording package is kind of a separate thing. You know, a big lush box set is sort of a different thing than, you know, just, you know, an album cover. So I'm guessing a lot of the new voters kind of made a push for this.

[Listener]

How has the visual identity of music changed in the streaming era?

[Joe Lynch]

I mean, that's a great question and a great point because, you know, you think of the 70s, you had these huge, you know, lush album covers. You know, I'm thinking Miles Davis, Bitches Brew, you know, this really surreal, gorgeous painting by Maddie Clarvine. You know, you were able to get a lot more detail on that. And then, you know, of course shrunk with the CD era, but you know, a cd, you can still kind of get a sense of stuff, but it got even smaller when, you know, everything went digital streaming. You might be looking at something that's just, you know, the size of your thumb almost, you know, if it's on your phone or Spotify or what have you. And to that, I think a lot of artists pivoted to these really simple, distinct designs. You know, you think of like Beyonce's self titled album is just, it's black and then all caps. Beyonce in pink. I mean, it grabs you, you know, grabs your attention even if it's tiny. Or Drake's. If you're reading this album cover, mixtape cover, it's just black text scrawled across white. And I think both of those. Or Taylor Swift's 1989, which is just kind of a Polaroid, pretty simple Polaroid with their head cut off. And those all share something interesting in common is that they went viral and they kind of felt designed to be imitated, designed that you were going to put that out and then someone was going to take Beyonce's name out and put their own name in that font or put little meme jokes in the Drake font and share that on social media. So something that's simple and kind of easy to, you know, memeify. Essentially.

[Listener]

Yeah, I was gonna ask, cause I've been thinking about the Serena Carpenter album cover release and the controversy around it. Is she a woman in control of her image or is she being sexualized? It was a really good piece and it was titled There were no winners in the Sabrina Carpenter debate on Social Media. Nuance is the enemy, but it doesn't have to be. I just thought that was a great headline.

[Joe Lynch]

I love that.

[Listener]

Right, so everyone, you can discuss for yourselves what you think about that cover. But I'm interested in the idea of social media influencing album cover art. What do you think?

[Joe Lynch]

Yeah, I think, I mean, absolutely. I think album covers are made with social media in mind. You know, I certainly don't want to say, you know, everyone, but that felt like an album cover that was meant to be dissected and meant to be argued over. You know, I think she knew she was being provocative. She knew that it would cause a discourse that divides even people who oftentimes agree, oftentimes people who are on the same side of the political spectrum. So it definitely felt like something that was meant to go viral, meant to cause debate and you know, and then people are talking about the record, which is a good promo. So yeah, I think social media has changed it. But you know, then you also risk there's the chance, well, if you really whiff it, you might get blowback. And before the album even comes out, people are just, you know, canceling you or whatever.

[Alison Stewart]

We're talking about a new addition to the Grammy Awards Best Album Cover category which will premiere in 2026. Joining us is Joe lynch, executive Digital Editor at Billboard. We're here to talk about the new category as well as the list of 100 Best Album Covers of all time. We've got some listeners who are weighing in. Best album cover or at least most memorable for college student Ohio players. Free youe Mind and you'd A will follow. You have to check on the inside cover. Okay, I remember that. Two favorite album covers. 1969, Black Sabbath by Black Sabbath, an eerie cover that helped usher in a new era of music, orally and visually. And then 1977, news of the World by Queen. A visual representation of a dystopian world using the band members likeness. Let's talk to Donna who's calling from Mount Vernon. Hi Donna, thanks for calling, all of it.

[Donna]

Wonderful to speak to you, my Alison. I can't believe I'm on the radio, but thank you.

[Alison Stewart]

Go for it.

[Donna]

Love your show.

[Alison Stewart]

Thanks.

[Donna]

Well, I picked two album covers. One is Abdullah Ibrahim's Water from an Ancient Well. It evokes some incredible jazz. My mother particularly loved this title piece and I love the album. There's a flow of water, there's some blue. I just love it. Okay. And then the other is reflective of my teenage years that came out in 1970. Cat Stevens. T for the Tillamon.

[Joe Lynch]

That's a fun one.

[Alison Stewart]

Thank you so much for calling. As a child, grew up in England, I was obsessed with the album cover for Super Breakfast in America, with the.

[Listener]

Diner waitress and the skyline on her tray. Stared at it for hours.

[Joe Lynch]

That's an iconic image.

[Listener]

Let's talk to Gabriel, who's calling from Brunswick, Georgia.

[Alison Stewart]

Hey, Gabriel.

[Listener]

Nice to talk to you.

[Gabriel]

Hey, Allison. Thanks so much, and hello to your guests as well. I just wanted to briefly talk about the COVID for Sticky Fingers by The Rolling Stones, 1971, designed by Andy Warhol and featuring a kind of cult figure in New York City, crotch Joe d' Alessandro, who's a really cool guy to look up. He's done a lot of film and other visual art, but the album featured a zipper on the front because it's a. It's a photograph of a pair of jeans. And in the shipping of these records, all those zippers, which were like pretty heavy duty zippers, they. They weren't able to lay the LPs flat against themselves in the boxes. So all those zippers ended up messing up all the LPs when they ship them out.

[Joe Lynch]

Interestingly enough, you know, I have a copy of that on vinyl, and I run into that same issue. I sort of have to store it separately because that zipper does press into the other records and kind of scuffs them up. But it's fun. You pull down the zipper and there's underwear behind it.

[Listener]

By the way, a text from our one person correcting another person's text. Free youe Mind and your blank will follow is by Parliament Funkadelic, not Ohio Players. Sorry about that. Let's talk about the artwork on the album that's interesting because we talked about the zipper in the Rolling Stones cover. What are the emerging trends, and how is AI factoring into album covers?

[Joe Lynch]

I mean, AI, that's such a big question. There's been some. If I get this wrong, I apologize. I believe KE had a single album cover that somehow used a bit of AI. It was mostly, you know, human design, but used AI somewhat. And then she got some social media blowback and ended up re releasing it without any AI. So, you know, I think right now we're at this point where fans, certainly graphic designers, certainly a lot of creative people are very suspicious of AI. And essentially, you know, if AI is used to create art, people are like, you know, that's it. You know, it's. The human element is out. It doesn't count anymore. This isn't real art. And, you know, honestly, I kind of probably skew towards that. But I think there's also this Pandora's box element with AI. You know, people younger than me are going to grow up with it and it's going to be part of their everyday lives in the way that, you know, radio changed civilization, you know, tv, online, all that stuff. So I do think, you know, 20 years from now, it's going to be. There'll be a lot of AI album covers, and people probably won't be blinking about it. But certainly at this point, you know, you do that, a major artist does that, they're going to raise eyebrows and get some flack for it.

[Alison Stewart]

We're talking to Joe lynch, executive digital editor at Billboard. We're talking about the Best album cover category, newly added to the Grammy Awards. After the break, we'll get into your list of the 100 Best Album Covers of all time. Listeners, what's your favorite album cover? 212-433-969. You're listening to all of it on WNYC. I'm Alison Stewart. My guest in studio is Joe lynch, executive digital editor at Billboard. He's talking to us about the new Grammy category best album coverage. And we also wanna talk to him because he made a list of 100 Best Album Covers of all time. You did this for Billboard. What was your criteria?

[Joe Lynch]

I did the criteria.

[Alison Stewart]

I did.

[Joe Lynch]

Well, it was 100. Yeah. You know, the criteria was to think of a combination of, you know, undeniably iconic images that kind of transcend the album. You know, people, even if someone's never listened to Abbey Road, which I know is unthinkable to some folks, you know, they know the Abbey Road cover. You know, the Velvet Underground is not the world's most popular commercially successful rock band, but people know the banana image. Same thing, you know, with the Sex Pistols album cover. I'm sure there's a lot of younger people who are very familiar with the look of it and the aesthetic of it, but, you know, probably couldn't name more than one song on the album or something like that. So there's that, you know, there's also this element of did it kind of push the art form forward as album art? Did it push fashion forward? Did it mark a turning point in that artist career? Did people start to look at the artist differently? And there's also just, I'll be honest, a little personal subjectivity in there. Some of these are just personal favorites. But I did, I consulted with our various Kind of genre leads on staff, folks in the country department, R and B, K pop, just to make sure. I was getting a diversity of sounds and eras in there. So there's certainly a couple of country albums on there that I'll be honest, if they hadn't suggested to me, I wouldn't have even thought to include. So I kind of canvassed our staff and pulled together what I thought was what I hope was a solid list. But I'll be honest, I look at it and I'm like, oh, how did I leave this off? How did I leave that off? So I could probably do 500.

[Alison Stewart]

It can evolve a little bit. Yeah. Let's talk about on your list, number 10 from 1994, the Notorious B.I.G.

[Joe Lynch]

Yes.

[Listener]

Ready to Die. Why'd you pick this?

[Joe Lynch]

That one is just, I think, such an, you know, I hate to overuse the word iconic, but it really is just like an iconic image for, you know, anyone who grew up with 90s hip hop. You know, it's this baby. I don't actually think it's a baby photo of him, but it's supposed to look like Biggie. You know, a baby with an Afro sitting there kind of in the distance on an all white background. And then the title, Ready to Die. You know, just the idea of, oh, my God, this is an infant. You know, this child hasn't even seen the world and already ready to die kind of gives you a sense of, you know, the gritty realism that, you know, Biggie was all about. But also there's a, you know, a teeny bit of humor to it. You know, it's a child on the hip or the COVID to a hip hop album, you know, with a lot of explicit content. There's a little bit of a smirk in there, too.

[Listener]

Let's take a listen to Biggie.

[Richard]

Put it to your headpiece, Run in the chamber the safety is off Release straight into dog homes I wanna see cabbage. Biggie Small the Savage Doing your brain cells much? Damn it. Teflon is the material for the Imperial Mic Ripper Girl Stripper, the Henny Sipper. I drop lyrics off and on like a light switch Quick to grab the right to make her drive the Q45.

[Listener]

I could just keep listening to that all day. Let's talk to Richard, who's calling in. Hi, Richard, you're on the air.

[Jeff]

Hi. Hi. How are you doing?

[Joe Lynch]

Great.

[Jeff]

I wanted to. I wanted to check in and see how many Roxy Music and Brian Cherry album covers you have, because starting at the first album they did, they went Completely against form of showing five glum guys with long hair. And showed a model. A model in stylish clothing with gold records, which went completely against what was being. Being done at the time. It was a nod to past records where, you know, someone like Ray Conniff would do a model on the COVID And the most iconic of those Roxy Music album covers is Country Life with the two semi clad women on it. That got so much controversy that they even released it in a green opaque plastic sleeve for a while.

[Joe Lynch]

You know, that is an iconic one. I have to. I'm glad you brought up Roxy, but I did end up choosing for your pleasure. Something about that one is just so, like, slinky and sexy and, you know, it's a mandolier on the COVID And who doesn't love an album cover with a mandalier? But those are all great Roxy covers, too.

[Listener]

Let's talk to Jeff from the East Village. Hey, Jeff, thanks for calling all of it.

[Jeff]

Hey, how are you doing?

[Joe Lynch]

Great.

[Jeff]

I'd like to mention Stand up by Jethro Tull. It's actually a wood cut from Jimmy Grashow. He did a bunch of album covers in the period. And if you look really carefully, the band member on the left has his hands clasped together and there's 11 fingers instead of 10.

[Joe Lynch]

That's before AI.

[Listener]

That's pretty good. Thanks for calling in with that little tidbit. This one says ODB from Wu Tang with his face on a New York stage. Food stamp ID card was incredible. Wish youh Were Here by Pink Floyd. Another Pink Floyd is a Dark side of the Moon. Allman Brothers. Eat a peach. Vinyl has the best art. All right, what was number one on your list, Jerry?

[Joe Lynch]

It was the Velvet Underground Iniko. You know which. The aforementioned. You know, it's the Banana. That one. It's Andy Warhol designed. Aside from being just a very indelible image that's kind of survived over the decades, even amongst people who aren't really familiar with their music at all. I chose that. There's this kind of interactive element to it. If you got the vinyl back in the day, there was a direction on the COVID saying, peel slowly and see. And you could peel off the yellow banana, peel, and under it was this kind of fleshy pink banana. Of course, Andy Warhol and Lou Reed both loved a phallic symbol, I got to say.

[Listener]

Let's talk to Richard in Brooklyn real quick. Hey, Richard. Richard. Oh, we didn't have Richard. Richard was a designer. I'll read his. He said he did the record for design. I Was a Teenage Zombie and it won a design. It was a theme song performed by the Flesh Tones and the others from the Submarines. So I'm sorry we couldn't get through to you. What's your favorite cover of all time? Joe?

[Joe Lynch]

My personal favorite, Cyndi Lauper. She's so unusual. It's just a beautiful explosion of color. It's a photograph by Annie Leibowitz. I think it's such a great example of a photographer bringing out the best in the artist. You know, the album cover is undeniably Cyndi Lauper's own style. You know, just the really bright in your face colors, you know, kind of the thrift store New York aesthetic. But Leibowitz frames it so perfectly. It's like everything in the frame, you know, it looks like, you know, it's a Stanley Kubrick movie or something. You know, nothing is out of place. Every color, every hue is exactly the color it needs to be. And I think it also just kind of sums up the, you know, the explosion of pop at the of that era of the 19, kind of 63, as it changed from new wave to, you know, what would become 80s pop that she helped usher in.

[Alison Stewart]

Joe lynch is executive digital editor at Billboard. Thanks for walking us through album covers.

[Joe Lynch]

Thanks for having me. How many discounts does USAA auto insurance offer? Too many to say here. Multi vehicle discount. Safe driver discount, New vehicle discount, Storage discount, Legacy. How many discounts will you stack up? Tap the banner or visit us aaa.com autodiscounts restrictions apply.

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