At the age of 19, Guy Oseary joined Maverick Records as an A&R executive, and then rose through the ranks to chairman, developing a roster of artists that included The Prodigy, Alanis Morissette, Deftones, The Wreckers, Paul Oakenfold, Michelle Branch, Summercamp and soundtracks on such film series as Austin Powers, The Matrix and Kill Bill. Oseary guided Maverick to sell over 100 million albums worldwide and secured its spot as one of the industry's leading boutique labels. As part of Maverick Films, Oseary executive produced Rob Zombie's first two ventures into feature filmmaking: House of 1000 Corpses and The Devil's Rejects; and four films of The Twilight Saga: Twilight, ', ', . He also serves as executive producer on NBC's Last Call with Carson Daly and New Year's Eve with Carson Daly. In May 2004, Guy Oseary partnered with Jason Weinberg and Stephanie Simon to become a principal in Untitled Entertainment, a management company with offices in Beverly Hills and New York City. In 2005, Oseary became the manager for his longtime business partner Madonna and guided her through the Confessions Tour, Sticky & Sweet Tour, and The MDNA Tour, which are among the highest-grossing concert tours of all time. He won Top Manager at the Billboard Touring Awards in 2006 and 2009. In 2007, Guy Oseary negotiated a 360 deal partnering Madonna with Live Nation worth $120 million. On 12 November 2013 it was announced that Guy Oseary would be replacing Paul McGuinness as manager of U2 in a $30 million deal which would see Live Nation buy both Maverick and U2's management company Principle Management. McGuinness was quoted as saying "I have long regarded Guy Oseary as the best manager of his generation, and there is no one else I would have considered to take over the day-to-day running of our business." Oseary is also the manager for Amy Schumer.
Other work
Guy Oseary has authored four books, including a book on Jewish influences in the music industry titled Jews Who Rock. His second book, On the Record, is a collection of first-hand accounts on how to break into the music industry from many of the most successful artists, producers and executives. He also authored two coffee table books with his own photography of Madonna's 2006 and 2008–09 tours respectively titled "Madonna: Confessions" and "Madonna: Sticky & Sweet." Oseary, along with Ashton Kutcher and Ronald Burkle, is a co-founder at A-Grade Investments, a venture capital firm that has made numerous investments in companies such as Airbnb, Foursquare, Shazam, SoundCloud, Spotify and Uber. In 2010, Madonna and Oseary founded gym chain Hard Candy Fitness. They've also partnered with Iconix Brand Group to launch the lifestyle brand "Truth or Dare by Madonna." Guy Oseary appears in cameos in movies such as Charlie's Angels, , and You Don't Mess with the Zohan. He also made a cameo in Madonna's 1992 music video for her single "Deeper and Deeper," in which he appears as a dancer with an afro wig in a club.
Charity
In honor of his 46th birthday, Oseary launched Good Today, a non-profit platform democratizing philanthropy and activism by making it easy and meaningful to give charity to hundreds of new causes and organizations across the globe.