Up until this fall, few people might utter the names U2 and Barry Manilow in the same sentence. Someone who rocks out to “Sunday Bloody Sunday” probably doesn’t also boogie to “Copacabana.” But in 2014, these two artists have much in common. They have both seen careers studded with platinum-selling records, conferring upon them substantial wealth and influence in the music industry. They are both, for lack of a better word, old. But most importantly, they both released new albums this fall that challenge existing conventions. U2’s release strategy and Manilow’s recording techniques raise important ethical questions about privacy, intellectual property and the acceptable limits of digital technology’s influence on recorded music.

On Sept. 9, U2 delivered Songs of Innocence onto our computers and phones. The band struck a multimillion-dollar deal with Apple to release the album for free to all iTunes users. It didn’t go entirely as planned: Frustrated users found it difficult to delete the album from their devices, fueling larger concerns over a twisted marriage of art and corporate leverage. The surprise release didn’t impress critics, either, who greeted the record with mixed reviews.

In an interview with The Seattle Times, the Black Keys’ Patrick Carney discussed the strange message the album sends to bands “that are just struggling to get by.” In an interview with Rolling Stone, Pink Floyd’s Nick Mason explained how the album contributes to the devaluation of music in the 21st century. And, most recently, in an interview with the Daily Mail, Sinead O’Connor said, “There was something almost terrorist about it.” In an age of growing concerns over privacy and surveillance, it’s easy to see why this surprise album rubbed people the wrong way.

For a while, I passively resisted the album. But I felt a journalistic responsibility to listen. In listening, I heard a return to the tried-and-true U2 formula: Bono’s anthemic “whoaaa”s, straight eighth-note bass lines, tons of reverb and lyrics like, “You’re breaking into my imagination / Whatever’s in there is yours to take.” Songs of Innocence doesn’t sound like something the whole world needs to hear, but diehard U2 fans might appreciate this watered-down version of sounds they have grown to love.

For better or worse, the release of Songs of Innocence managed to defy the expectations of millions of people and has made a sizable impact. A band that was releasing platinum albums more than 30 years ago has elicited the biggest reaction from the general public in its career. The release also taught us an important lesson: This is what happens when we agree to the terms and conditions of iTunes without reading them. Seriously: We don’t actually own our iTunes libraries. Apple does.

Other aging artists, including several who were popular in the ’60s and ’70s, have released new albums in which they perform covers of songs they love. These projects tread a thin line between earnest and indulgent. To name a few: In 2000, Joni Mitchell released Both Sides Now, on which she sang jazz standards and reimagined some of her original works. In 2004, Brian Wilson released an album titled In the Key of Disney, performing his favorite hits from Disney films. In 2009, Bob Dylan released Christmas in the Heart. And in 2010, Carlos Santana released Guitar Heaven: The Greatest Guitar Classics of All Time, where he jammed along to his favorite riffs. Seventy-one-year-old Barry Manilow’s latest album, My Dream Duets, takes this strange genre to new and questionable heights.

Manilow doesn’t just recreate his favorite songs from the past; he inserts himself into them. He sings alongside a diverse group of artists, making immediate and jarring transitions from Whitney Houston to John Denver, for example. The only theme running through the entire album is that the artists behind the original recordings are dead.

Yet Manilow shares the stage with the original performers. Thanks to modern technology and licensing, his dream has become a haunting reality. Manilow’s reverence for legends of the past takes the combination of earnestness and indulgence to a new level. He is living every fan’s dream, but because of his wealth, he is also benefiting from recordings that do not belong to him.

Songs of Innocence and My Dream Duets are revolutionary in that U2 and Manilow both managed to do something completely original. Each introduces new possibilities for the production and distribution of recorded music. Ethical concerns aside, I can appreciate where these releases are coming from. U2 and Manilow are responding to what they see as a serious problem in the contemporary music industry: As music becomes more accessible and readily available, the relationship between artists and listeners diminishes.

In U2’s case, what many saw as an invasive release strategy had benevolent intentions. By abolishing commerce, a typical separation between artists and listeners, U2 thought they were simply sharing their newest work, an admirable act. Unfortunately, many felt they were being force-fed.

Manilow attempts to connect to his audience in a different way; on the album, he is just another fan who gets to sing with his idols. In a convincingly edited artificial conversation with Jimmy Durante on the album’s first track, he asks, “I mean, what chance do I have singing duets with all these legends?” Durante assures him, “It’s gotta come from the heart!” as they break into song together. He also moans, “Sing to us Whitney!” after his duet of “I Believe In You And Me” with Whitney Houston. Manilow playfully brings himself down to the listener’s level. Unfortunately, the listener is unlikely to see the album on Manilow’s terms. Similar duet projects have been done before, but mostly by family members of late musicians; Frank Sinatra and Elvis Presley come to mind. Here, however, Manilow’s only relationship to his fallen heroes is his wallet. And frankly, listening to these tracks only directs me to listen to the originals and appreciate them for what they are.

Technological changes necessitate new approaches to the production and distribution of music. As new possibilities emerge, artists will continue to experiment with original ways to connect to their fans. For better or worse, I imagine that innovations like these albums will continue to be released in coming years. While Manilow and U2 managed to push boundaries in ways that are disconcerting, they have pushed boundaries nonetheless.