Which artists have performed at the Super Bowl halftime show more than once?

One of the defining features of the Super Bowl, which sets it apart from the other major sports finals, is the halftime show. The 15-minute musical interlude is one of the biggest attractions of the event, featuring the stars of the day. During the early years, and for most of the first decade, a college marching band provided musical entertainment at the interval. Later, Up with People (UWP) got involved. Guests were usually from the jazz world - Ella Fitzgerald, Doc Severinson, Lionel Hampton and Anita Bryant were among the more well known entertainers invited to perform during the 1970s.

It wasn’t until the early 90s that popular music came to the fore. New Kids on the Block were the first pop act to headline, performing a couple of their hits at Super Bowl XXV in 1991. The move towards younger, chart-topping artists with a fresher appeal helped to boost dwindling television audience figures and during the last 33 years, several artists have appeared more than once.

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Gloria Estefan, the artist to have appeared the most at the Super Bowl halftime show

Miami Sound Machine singer Gloria Estefan is the artist to have made the most appearances at the Super Bowl halftime show. The La Havana-born, eight-time Grammy winner made her debut appearance in the Winter Magic production at the XXVI edition in Minneapolis in January 1992. The singer took to the stage for the last five minutes, treating spectators to two of her self-penned hits: Live for Loving You and Get on Your Feet.

She was back three years later - this time bringing her band with her. Miami Sound Machine were invited guests for the Disney-produced, Indiana Jones and the Temple of the Forbidden Eye halftime extravaganza, joining Patti Labelle and Tony Bennett on the main stage in Florida.

Estefan’s last Super Bowl performance was in also in her hometown Florida - the city her family fled to when she was just a baby. ET flicked the switch to turn on the lights for the Super Bowl XXXIII halftime show where headliner Stevie Wonder was chauffeured in singing Sir Duke. Estefan appeared halfway through the segment, delivering a blistering, timbale-led latin workout - Oye Mi Cuerpo Pide Salsa followed by a cover of Vicky Sue Robinson’s 1976 disco anthem Turn The Beat Around. Stevie Wonder joined her for the finale - a medley of both of their hits: You’ll Be Mine (Party Time), Another Star and My Cherie Amour”.

Gloria almost made a fourth appearance. She explained why she turned down the chance to perform alongside Jennifer Lopez and Shakira at the 2020 Super Bowl as the limited running time wouldn’t allow all three to showcase their hits: “I literally would have come out, Come and Shake your Body - out!”

In total, four artists have performed more than once at the halftime show - either as the headline act or special guest. Justin Timberlake, Nelly and Bruno Mars have all performed twice - Timberlake’s 2004 act going viral for Janet Jackson’s infamous wardrobe malfunction. This weekend, they will be joined by this year’s headliner Usher, who made his first appearance back in 2011 when the Steelers and the Packers scrapped it out for the title in Arlington, Texas. On that occasion, he only had a cameo role, singing just one song OMG, a duet with will.i.am.