By November 1985, Madonna was everywhere. Her album Like a Virgin had produced back-to-back hits, “Crazy for You” reached number one, and her film Desperately Seeking Susan proved she could act. TIME Magazine put her on its cover in May. In August, on her 27th birthday, she married actor Sean Penn, making their relationship front-page news. Even Playboy’s September issue — which published old nude photos — kept her name in circulation. She was one of the most talked-about people in the country.
Saturday Night Live tapped Madonna to open its eleventh season on November 9, 1985. Her role that night was strictly as host and comedic performer — she did not sing. Simple Minds served as the musical guest, riding high on “Don’t You (Forget About Me).” Madonna wouldn’t perform on SNL as a musical act until January 1993.
The opening monologue set the tone. Madonna addressed her whirlwind year directly, using her very recent marriage to Sean Penn as comedic material. The season 11 cast she worked alongside that night included Randy Quaid, Joan Cusack, Robert Downey Jr., Jon Lovitz, Dennis Miller, Nora Dunn, Danitra Vance, Terry Sweeney, and Anthony Michael Hall.
One sketch placed Madonna inside the White House. She played Princess Diana in a parody of a royal visit to President Ronald Reagan and First Lady Nancy Reagan.
The sketch took its structure from Who’s Afraid of Virginia Woolf?, casting Jon Lovitz as Prince Charles alongside Madonna’s Diana. The night also included a sketch called “Pinklisting,” which tackled Hollywood’s growing fear around the AIDS crisis.
Madonna also appeared in “National Inquirer Theatre,” channeling Marilyn Monroe opposite Anthony Michael Hall as Bobby Kennedy and Randy Quaid as President John F. Kennedy.
In another segment, she played a character named Marika in a Latin-flavored sketch called “El Spectaculare De Marika.”
She also stepped outside the scripted sketches to assist the magic duo Penn & Teller during their guest performance.
The musical surprises weren’t limited to Simple Minds. Madonna performed a Latin-style cover of A-ha’s “Take On Me,” with backing vocals from Jon Lovitz, Damon Wayans, and Robert Smigel.
She also appeared as herself on the recurring sketch “The Pat Stevens Show,” where Nora Dunn’s passive-aggressive talk show host interviewed her — letting Madonna play on her own public persona within the comedy format.
