Gwen Stefani, Diddy, Apple’s Tim Cook and others will have to choose which music mogul’s soiree they will attend.

Music's second-biggest night is supersized this year as the annual Clive Davis pre-Grammy party (sponsored by the Recording Academy and honoring manager Irving Azoff with its Salute to Industry Icons Award) and Apple executive Jimmy Iovine's wedding to Liberty Ross (ex-wife of movie director Rupert Sanders and sister of Gone Girl composer Atticus Ross) are both scheduled to start within an hour of each other on Valentine's Day. (The Grammy Awards air live on CBS on Feb. 15.)

While logistically the nuptials at David Geffen's Beverly Hills mansion and the annual A-list soiree held at the Beverly Hilton are mere miles apart, industry veterans are quick to note the metaphorical distance: Azoff and Geffen were known archrivals dating back to the 1970s when the then-upstart rep and the erstwhile young label boss sparred over the Eagles, a feud well-documented in books and even the band's own 2013 doc, History of the Eagles.

To be fair, the Grammy team did try to move Davis' sold-out party to Saturday, Feb. 13, but the hotel had a previously booked event that evening (and it's unlikely the Davis bash would have gone up against the annual MusiCares Person of the Year event, also presented by the Recording Academy), while Iovine has told friends it was his bride-to-be's wish to get hitched on Valentine's Day. Still, allegiances to both music biz legends promise a busy night for the likes of Gwen Stefani (signed to Interscope by Iovine and managed by Azoff) and Stevie Nicks (Iovine's protege and former girlfriend and a client of Azoff's via Fleetwood Mac), who'll have to party-hop. (Fortunately, Davis' has a reputation for running long past midnight.)

While some power players are coy about their Feb. 14 plans (cracks Universal Music Group chairman Lucian Grainge: "Jimmy knows where I'll be"), one insider holding a coveted invite to both tells THR: "A wedding is a once-in-a-lifetime thing; Clive's happens every year." Indeed, even Irving and Shelli Azoff plan to stop by and congratulate the happy couple.

Reps for Davis, Iovine and Azoff did not comment nor would they confirm the guest list, but The Hollywood Reporter has surveyed various industry players and surmised that the evening will go something like this:

Attending the Iovine-Ross wedding: Trent Reznor, Atticus Ross, Dr. Dre, Eminem, Kanye West and Kim Kardashian, Mick Jagger, Oprah Winfrey and Gayle King, Sheryl Crow, Bruce Springsteen, Mary J. Blige, Tom Petty, Bono, Maroon 5 manager Jordan Feldstein, Lady Gaga

Attending the Clive Davis & The Recording Academy 2016 pre-Grammy Gala: Jon Bon Jovi, Jennifer Hudson, Recording Academy president Neil Portnow, Sony/ATV Chairman Martin Bandier, Meghan Trainor, Diane Warren, John Legend, Larry King, Christina Aguilera, Nile Rodgers

Pulling double-duty: Stevie Nicks, Gwen Stefani, Sony Music CEO Doug Morris, Apple's Tim Cook and Eddy Cue, Miley Cyrus, Universal Music Group chairman Lucian Grainge, Epic Records chairman L.A. Reid, Diddy, Taylor Swift, Jennifer Lopez, Patti Smith, Enrique Iglesias, members of Van Halen