The championship game in the National Football League, named the Super Bowl, is a massive event of substantial cultural significance in the US. Traditionally, over a hundred million Americans tune in to watch it, making it the most viewed thing each year on TV screens throughout the nation. And in its close to six-decade existence, the commercials featured during it and its halftime show have become equal attractions for mainstream audiences as the football game whose viewers they utilize.

Before the 1990s rolled around, the Super Bowl was still a mega event, but it was not as commercialized as it is now. In the future, with the federal sports wagering barrier in America falling in 2018, fans can expect the last game of the NFL playoffs to see even higher degrees of exploitation. No doubt, operators will soon be competing to advertise their platforms as the best site to bet on Super Bowl action.

Again, prior to the start of the 1990s, or 1991 to be precise, halftime entertainment at the NFL championship game was usually a responsibility of university marching bands. That changed when New Kids on the Block took up this role at Super Bowl XXV in Tampa. From that point on, the position of halftime entertainer became coveted. So much so that Michael Jackson assumed it in 1993, and before the decade concluded, the likes of Diana Ross, Steve Wonder, ZZ Top, Teddy Pendergrass, and Patti LaBelle graced the Super Bowl stage.

Below, we rattle off what many consider the five best and most important Super Bowl halftime performances, in ascending order, listed by the year they happened.

1967 – The University of Arizona Symphonic Marching Band

It seems fitting to kick off this list with the initial Super Bowl mid-game show. In the first three decades following this event’s birth, the entertainment fans got presented sizably differed from what they get now. As mentioned, before 1991, few famous music artists participated in the provided halftime distraction. As a rule of thumb, the performances came from marching bands, drill teams, and groups like Up with People. Carol Channing, in 1970, can get classified as the first celebrity to perform in the Super Bowl halftime show.

But, at the conclusion of the 47th regular season of the National Football League, the one with the first Super Bowl. Where the Green Bay Packers defeated the Kansas City Chiefs, the entertainment beginnings were humble. The simulcast aired on NBC and CBS included the University of Arizona Symphonic Marching Band as the headliner, with appearances from trumpeter Al Hirt, the Grambling State University’s Marching Band, and the Anaheim High School drill team. In general, the first Super Bowl halftime show was a tribute to US history and a device to introduce the league’s newly-founded teams.

1991 – New Kids on the Block

For those not up on music history, New Kids on the Block were among the first sets of boy bands to kick off this craze. They enjoyed substantial success in the 1980s and early 1990s, selling around eighty million records globally. Most people credit them as laying the groundwork for the emergence of other worldwide pop group phenomena like NSYNC, the Backstreet Boys, and Take That.

1991 was the final time the Super Bowl would get held at Tampa Stadium. It marked an end of an era. Unfortunately, ABC decided not to televise, live, the New Kids on the Block show. Instead, the station opted to broadcast an in-progress Gulf War report, saving the band’s performance for a tape delay shown after the game. Nevertheless, their execution of hits like This One’s For the Children and Step by Step on this Walt Disney-sponsored event signaled a new direction that Super Bowl would take going forward concerning halftime fun. That seemed fitting, as this was its milestone twenty-fifth edition.

1993 – Michael Jackson

Dubbed the King of Pop, no person was more famous than Michael Joseph Jackson in the 1980s and 1990s. 1993 was a massive year in MJ’s career, as the artist embarked on his Dangerous World Tour, and for the first time, child sexual abuse allegations got made against him. However, in January of that year, he got invited to perform at Super Bowl XXVII in California (Pasadena) to help the game’s attendance and viewer figures. Ironically, this event became the first in NFL history where the half-time show got more eyes on it than the Championship match.

In his stunning performance, Jackson rendered versions of Billie Jean, Jam, Heal the World, We Are the World, and Black and White to massive crowd reactions.

2004 – Janet Jackson & Justin Timberlake

Janet Jackson may not have been at the height of her career in 2004. Yet she was coming off her appearance in the Eddie Murphy hit Nutty Professor II: The Klumps and All for You, and Justin Timberlake was red hot on the heels of his debut solo album Justified. The pair teamed on the Take Me Now song at Timberlake’s request. And they got asked to perform at Super Bowl XXXVIII in Houston.

Sadly, their appearance and showing do not get remembered as a display of musical talent. But for a wardrobe malfunction that left Jackson’s naked breast getting exposed to one hundred and forty million viewers. It likely ranks as the most infamous Super Bowl halftime show incident.

2007 – Prince

Without question, quality-wise, the best-reviewed, and most-enjoyed halftime Super Bowl show was one from The Artist Formerly Known as Prince, who brought the house down at Super Bowl XLI at the Hard Rock Stadium in Miami backed by a brass marching band.

Prince not only did many of his classics like Purple Rain. He also performed mash-ups of All Along the Watchtower and Proud Mary. Many considered Prince a curious choice. Nevertheless, the eccentric artist proved all doubters wrong via an electrifying performance that still gets talked about. Rolling Stone magazine described it as an example of total mastery, a legendary Prince moment, and the best Super Bowl show of all time.