Today in Madonna History: November 3, 2000

November 3, 2026 By Jay in 2000, October Tags: David Letterman, Don't Tell Me, Firsts, Live Videos, Monte Pittman, Music (Album), TV Performance 1 Comment

On November 3 2000, Madonna guested on CBS-TV’s Late Show With David Letterman to promote the Music album. She performed an acoustic version of the album’s second single, Don’t Tell Me.

The performance featured several firsts for Madonna: her first live performance to promote the Music album; her first TV appearance following the birth of her son Rocco; her first performance on guitar since her pre-fame days in NYC band Emmy; her first unplugged/acoustic live performance; her first live performance with longtime guitarist Monte Pittman; and her first (and only) musical performance on the Late Show.

Despite being promoted as such, it was not, however, Madonna’s first time back to the Late Show after her infamously censored 1994 appearance. She had made a brief, unscheduled visit to the set to drop off a valentine for Letterman during a 1995 taping of the show.

Today in Madonna History: August 28, 2003

August 28, 2026 By Jay in 2003, August Tags: Britney Spears, Christina Aguilera, Hollywood, Into the Hollywood Groove, Kiss, Like A Virgin (Single), MTV Video Music Awards, Radio City Music Hall, TV Performance, VMA's 1 Comment

On August 28 2003, Madonna performed Hollywood with Britney Spears and Christina Aguilera as the opening number for the 20th annual MTV Video Music Awards at Radio City Music Hall, New York, NY and upstaged everyone at the ceremony when she shares a passionate open-mouth kiss with them. Missy Elliott also joined the ladies on stage – post-kiss.

Madonna commented on the uproar surrounding the infamous kiss during an appearance on Oprah several weeks later. “I don’t know why people are making such a big deal about it,” she said. “Hasn’t anyone seen two girls kiss before? It was a friendly kiss – it really was. If Britney looks as though she is kissing me in an aggressive way it was a surprise to me.” She added, “I’m a showgirl. After 20 years in the business, we learn to roll with the punches. If someone’s coming at you with lips slightly parted, you kiss them.”

Today in Madonna History: June 2, 2005

June 2, 2026 By Jay in 2005, June Tags: Benefit Concert, Like A Prayer (Single), Live 8, Live Videos, Music (Single), Ray Of Light (Single), TV Performance 1 Comment

On June 2 2005, Madonna.com confirmed Madonna’s participation of Live 8:

“Sir Bob Geldof confirmed in a press conference yesterday the details and confirmed the artists featuring in Live 8 – a series of five live shows in London, Paris, Philadelphia, Rome and Berlin on Saturday July 2nd. The concerts have been organized by Bob Geldof and Midge Ure as part of a campaign to force the world’s richest nations to relieve poverty in the third world. The concerts – which will be free – are aimed at raising awareness of poverty just before leaders of the Group of Eight industrialized nations meet in Scotland…”

Madonna went on to perform a three-song set from London’s Hyde Park consisting of Like A Prayer, Ray Of Light & Music.

Today in Madonna History: February 13, 1995

February 13, 2026 By sonicboy19 in 1995, February Tags: David Letterman, Interview, Late Show, TV Performance, Valentine's Day 1 Comment

On February 13 1995, Madonna made a surprise appearance on CBS-TV’s Late Show with David Letterman.

In her first visit back to the Ed Sullivan Theater after her controversial 1994 appearance, Madonna presented Letterman with a Valentines Day gift.

And no, it was not her underpants…

Today in Madonna History: February 12, 1984

February 12, 2026 By Jay in 1984, February Tags: Borderline, Christopher Ciccone, Holiday, The Dance Show, TV Performance 1 Comment

On February 12 1984, Madonna was featured on The Dance Show, a syndicated American television variety show.

She appeared in a segment from New York performing Holiday and Borderline, followed by a brief interview in which she introduced her brother and backup dancer, Christopher. Borderline was also included in a second episode that aired a few months later on April 25th, as the single was climbing the charts.

Despite an extensive list of promotional appearances for her first album, this was Madonna’s only known television studio performance of Borderline until she revisited the song during a 2016 appearance on The Tonight Show with Jimmy Fallon.

Today in Madonna History: February 8, 2015

February 8, 2026 By Jay in 2015, February Tags: Grammy Awards, Live Videos, Living For Love, Take A Bow, TV Performance 1 Comment

On February 8 2015, Madonna performed Living For Love at the 57th Annual Grammy Awards. The ceremony was held at the Staples Center in Los Angeles, California.

Hitfix.com considered Madonna’s performance to be one of the best at the 2015 Grammys:

Madonna recruited the muscle-bound minotaurs from her Living for Love video for her Grammy performance of the new single, and she proved she was still a charismatic gale-force as a performer. Twenty years after she played the jilted wife of a matador in her Take a Bow video, Madonna’s now the show-running matador waving a cape at horned gents.