January 29 – Madonna announces that she will extend her record-breaking Sticky & Sweet Tour during summer 2009, to visit cities that were excluded during the first run. The tour kicked off at The O2 in London on July 4. The extension took the Sticky & Sweet Tour to a total of over 80 shows, putting it among the top five tours of all time.[7]
R&B singer Chris Brown is arrested after he physically assaulted his then girlfriend, Rihanna. He is charged with assault and making criminal threats, and received five years of probation.
February 18 – Flo Rida breaks his own record when his single "Right Round" is downloaded 636,000 units in the opening week. His 2008 chart-topper "Low" set the previous record for most downloaded song with 467,000 units sold in the first week of release.[15]
March 11 – Tickets go on sale for Michael Jackson's This Is It series, 10 shows extended to 50 shows and impressively all 50 dated sold out in under four hours making them the fastest selling concerts ever in history.
April 4 – The 2009 Rock and Roll Hall of Fame induction ceremony takes place, welcoming new inductees Little Anthony & The Imperials, Bobby Womack, Run-D.M.C., and Metallica. Metallica, citing the drama surrounding Blondie, Black Sabbath, and Van Halen's inductions, includes Cliff Burton and Jason Newsted both former bassists for the band in the induction.[18] Newsted also performs with band in its first rendition as a 5-piece band featuring two bass guitarists.[19]
April 12 – Carrie Underwood's "I Told You So", from her album Carnival Ride, becomes her tenth straight number one in the country songs chart, making her the only country artist in history to have their first 10 singles reach number one.
April 27 – Creed announces their reunion, new album and tour after a five-year break. They break up for a second time in 2013, only to reunite again in July 2023.
Roughly two weeks before his This Is It series of concerts is scheduled to begin, Michael Jacksondies in his Los Angeles home of an accidental overdose of propofil and benzodiazepines, later discovered to be the result of medical malpractice by his personal physician, Conrad Murray. The American music icon's passing triggers a surge in posthumous sales making him the best selling artist of the year, with 35 million albums sold worldwide in the months following his death.[23][24]
July 13 – Lady Gaga becomes the first artist to have three songs from a debut album to reach number 1 on the Billboard Hot 100 since Fergie's The Dutchess.
July 17-21 – Paul McCartney performs three sold-out concerts at Citi Field to open the stadium with opening act, The Script. This is because on August 15, 1965, The Beatles performed the first concert at Shea Stadium and McCartney joined Billy Joel on stage a year ago for the last concert there. Joel joined McCartney again on the first night.
August 8 – Meghan Lindsay and Josh Jones of Steel Magnolia won the second season of CMT's Can You Duet. Brandon Green and Jonathan Cox of JB Rocket were named runner-up.
October 15 – Britney Spears's "3" enters the Billboard Hot 100 at number one, her third number one on Billboard Hot 100 and the first non-American Idol related single to enter the chart at number one since 1999.[30]
October 28 – Michael Jackson's This Is It, featuring behind the scenes footage in the days before his death, is released. It enters the chart at No. 1, and becomes the best selling documentary of all time, raising over $250 million.