Risk (1999–2000)

Following the band's first real radio success with Cryptic Writings, Megadeth opted to again work with country pop producer Dann Huff in Nashville on their eighth studio album, which began in January 1999. The writing of the album was again supervised by manager Bud Prager, credited with co-writing on five of the album's twelve songs. Prager convinced Mustaine to grant producer Dan Huff more control over the recording process. "When it comes to Risk", Mustaine later wrote, "there'd been people in there playing and I wouldn't even know who they were or where the parts came from, and I'm not used to that. I was a little bit intimidated by the success we had with Cryptic Writings, so when it came to creating new material after that, it's like being "power-drunk" - you want more. After the success with "Trust", I thought to myself "wow, we've had a number one hit." We'd had four top five hits in a row, so why would I not want to give Dan even more control when it comes to the producing part on the next record? So I did, and it backfired."

Released on August 31, 1999, Risk was both a critical and commercial failure, and led to a backlash from many longtime fans. Although recent Megadeth albums had incorporated mainstream rock elements alongside a more traditional heavy metal sound, Risk was virtually devoid of metal, featuring instead dance, electronica, and disco influences. Risk was Megadeth's first release since 1985 not to be certified gold or higher in the US. The album's lead-off single, "Crush Em", appeared on the Universal Soldier: The Return soundtrack, temporarily as World Championship Wrestling's entrance theme for Bill Goldberg and later became an official NHL song, played during hockey games. Singles were made out of Crush 'Em, Breadline and Insomnia.

In July 1999, Megadeth recorded a cover version of the Black Sabbath song "Never Say Die", which appeared on the second Nativity in Black tribute album. They began their world tour in support of Risk in September 1999, playing alongside Iron Maiden during the European leg. Three months into the tour, longtime guitarist Marty Friedman announced that he would be leaving the band, citing musical differences. As Mustaine later explained: "I told (Marty) after Risk that we had to go back to our roots and play metal, and he quit." Megadeth enlisted guitarist Al Pitrelli, formerly of Savatage, Alice Cooper, and currently of Trans-Siberian Orchestra, as Friedman's replacement in January 2000.

Megadeth returned to the studio in April 2000, to begin work on their ninth studio release. However, one month into production the band was given the opportunity to join the "Maximum Rock" tour, alongside Anthrax and Mötley Crüe. Megadeth put the recording on hold, and toured North America throughout the summer of 2000. Early into the tour, Anthrax dropped off the bill, allowing Megadeth to play an extended, co-headlining set.

Megadeth and Capitol Records parted ways in October 2000, after fourteen years. The label returned the band's newest recordings, and in return released a greatest hits record, Capitol Punishment: The Megadeth Years. The album also featured two new tracks, "Kill the King", and "Dread and the Fugitive Mind", both of which showcased the band's return to their metal roots following Risk.