Hitmakers of the late '90s and '00s are touring together. Why experts say ‘nostalgia tours’ are a ‘win-win’ for the whole family.

Those longing to relive a time when pop anthems were burned onto CDs and MTV’s Total Request Live was must-see television are living their own teenage dreams.

Several so-called "nostalgia tours" are underway, reuniting chart-toppers of the ‘90s and early ‘00s whose music defined the soundtrack of a generation. The formula is a win-win for fans who get to experience a virtual mixtape of their favorite artists all in one place.

Rap icon Missy Elliot recently announced her first-ever headlining tour, Out of This World: The Missy Elliot Experience. While Elliot is the main attraction, she isn’t basking in the spotlight alone. The 24-date run will tour across North America this summer and feature Ciara, Busta Rhymes and Timbaland, all of whom are music legends in their own right.

Last fall, hip-hop stars Ludacris, Ashanti, Ja Rule, Nelly and more had fans screaming, “It’s getting hot in herre,” when they toured several cities for their My 00's Playlist concert series. Global powerhouses Enrique Iglesias, Ricky Martin and Pitbull also capitalized on the trend with last year’s The Trilogy Tour, which recently added 18 new stops across North America this summer.

Meanwhile, iconic boy band New Kids on the Block announced the Magic Summer 2024 tour, featuring singer-dancer Paula Abdul and DJ Jazzy Jeff, who is known for producing ‘90s hits like “Gettin’ Jiggy Wit It” and the theme song to Fresh Prince of Bel-Air, both performed by Will Smith.

These tours are about more than just nostalgia. As experts explain to Yahoo Entertainment, they’re a testament to the lasting impact of a pre-digital music era and the deep connection to a time when music connected us without phone screens.

What’s behind the trend?

Concert ticket prices are soaring, and insiders say these tours are far more affordable to consumers because they can see multiple artists at one event, and that venues view these “festival-like” experiences as less risky.

“It's more economical to go to a concert with multiple artists there, and I think the artists themselves recognize that,” Joycelyn Wilson, a professor of Black media studies and hip-hop culture at Georgia Tech, told Yahoo Entertainment.

“The last thing an artist wants to do is to have to cancel a concert tour because they're not selling tickets,” she explained. Jennifer Lopez, for example, had to rebrand her tour due to poor ticket sales. “Artists who are choosing to go on tour together know they have a fan base, and they know they’ll sell tickets.”

The advent of streaming and social media, Wilson argued, has distorted the idea of star power and which artists are likely to fill stadiums.

“There is a bit more blurriness with streaming numbers because we know some of those numbers are inflated,” she explained. “You may be an artist that streams well on TikTok, for example, but you might not be able to sell tickets for a live concert.”

Lucas Keller, president and founder of Milk & Honey, which manages top songwriters and producers in the music industry, said nostalgia tours are a “win-win” for everyone.

“The value of packaging these acts together can really be a 1+1+1 = 10,” he told Yahoo Entertainment. “Oftentimes there are tour packages of acts who only had one or two hits, so the consumer gets to hear an evening of hits across multiple acts instead of one superstar.”

Legacy artists are able to capitalize in ways they might not otherwise have the opportunity to, he added. Fans are spending big money on meet-and-greets as well as merchandise, which they may not have been able to afford during the heyday of the ‘90s, when they had less disposable income.

Not to mention, streaming services disrupted profits that once came with record sales and residuals from radio play, said music industry strategist Sarah Jones, which has made touring a prerequisite.

“All artists, legacy and new, have seen such a dramatic drop in recording sales that live shows are where they're earning the bulk of their money these days,” she told Yahoo Entertainment. “Touring packages capitalize on combined fan bases, nostalgia and the spending power of older audiences.”

Reinvent and reclaim

The new trend arrives on the heels of a ‘90s renaissance in TV, music and fashion, which Wilson said is a reflection of something deeper.

“Everything is digital; everything is intangible now,” she explained. “The ‘90s and early 2000s represents a moment where you went into the record store and bought your music. It represents a time when things were tangible — tickets were tangible, merchandise was tangible. Now, you put up your phone and scan [your ticket] at the door.”

To that end, stars like Missy Elliot, Ludacris and Enrique Iglesias aren’t exactly reinventing themselves with these tours, she added. Rather, they’re re-introducing themselves to fans who were there at the beginning when their music was its most authentic.

That’s something many artists have traditionally steered away from, Keller explained, noting that most performers are pressured to put out new music as much as possible to stay relevant.

“Many acts, as they age, are reluctant to play their hits and want fans and the industry to focus on new music,” he said. “I think some people have a good sense of humor about things and lean into their past, which is a good thing. In most cases, new albums are made just to support the tour, and new hits don’t tend to come from those releases anyway.”

Nostalgia tours also allow artists to not be pigeonholed in the decade their music was released, Keller explained, giving them the ability to remain in the zeitgeist for as long as possible.

“Nostalgia tours are targeting initial fans who are now older but want to relive the hits and the ‘90s experience,” Keller explained. “For boy bands and artists that had a fanatical pop audience in their younger years, these fans are still engaged and want to relive that experience.”

With hip-hop celebrating its 50th anniversary, Wilson said tours provide fans with historical reflection and opportunities for artists to rope in a new generation of listeners.

“What we're seeing is the potential to have this music expand across generations in the same way that, say, rock and country does,” she said of the value of nostalgia tours. “That’s something that brings in the entire family, making their music timeless.”

It’s not just Missy and Ludacris, either.

“Folks like the Roots, Digable Planets, these are folks that put out their first albums in their early 20s and are now in their mid-50s and still on the road touring,” Wilson said. “There will always be a market for their fans. Collaborating in this way adds to their legacy.”