Despite numerous hiatuses and the brief departure of founding member and lead guitarist Kyle Cook from the group, Matchbox Twenty has organized a tour that, according to drummer Paul Doucette, “was always going to happen.” Joining together for a double headline show with Counting Crows—the alt-rock group celebrated for 1993 anthem “Mr Jones” and Shrek 2 soundtrack staple “Accidentally in Love”—the two bands will throw down classic hits from their back catalogues at Rogers Arena on Sunday (July 16). With a collective 48 years in the industry under their belts, there’s plenty to learn about the two '90s staples.

1. Who needs a backup plan? Assuming you don’t mind living in your parents’ broom closet at age 40, rolling the dice on music stardom without a fallback career is a huge gamble. That didn’t stop Matchbox Twenty frontman Rob Thomas from doing just that. Last August he told the Onion AV Club that back when back when the band was struggling to get off the ground he quite intentionally took “every shitty job that couldn’t become a career”, including making futon beds.

2. Thomas’s 1999 collaboration with Santana, “Smooth”, is quite literally one of the most popular songs of all time. Billboard ranked it the number-one Hot 100 song of the ’90s, and the number-two Hot 100 hit of the 20th century. “Smooth” won three Grammys and helped earn Thomas the BMI award for Pop Songwriter of the Year in ’99. The funny thing is, Thomas never intended to record the vocals himself—he wrote the lyrics with George Michael in mind, but when Carlos Santana heard the Matchbox Twenty frontman’s demo of the song, the legendary guitarist asked Thomas to sing it.

3. Despite creating music that errs on the softer side, Thomas grew up as a bona fide badass. Spending his teenage years as an acid, weed, and coke enthusiast, the singer once did two months in jail for stealing a Camaro. All that changed when he met his wife of 18 years, Marisol, who calmed his excessive boozing and drug habits—but the union lost him some street cred. According to Rolling Stone, when Thomas first met Keith Richards, he hoped the rockstar might be positive about his music. Instead, Richards said leeringly, “Oh, you’re the one with the wife.”

4. In 2008, Counting Crows singer Adam Duritz wrote an article for Men’s Health magazine detailing his struggle with dissociative disorder. A few years prior, it had gotten so bad that the frontman felt he had lost touch with reality. Determined to change his life for the better, Duritz got on the right medication and started eating right and exercising. He also wrote Saturday Nights and Sunday Mornings, which is regarded by many as one of Counting Crows’ most visceral and cathartic albums.

5. Dread dred: Considering that Duritz is 50 and sports massive black dreadlocks that suggest Sideshow Bob crossed with a tarantula’s legs, it’s no shocker his hair isn’t real. In 2009 he suggested they were extensions, explaining in the Independent in Ireland that he tried growing the real thing but “they itched and smelled bad”. That’s at least progress from 2004 when he told the New York Post that his ’do was a wig given to him by his dad, explaining “My father, who's a Jewish doctor, went bald so he wore this and he gave it to me to wear."