Ever Since its inception in 1988, we have seen a SummerSlam event every year. Known as "The Biggest Party of the Summer", It is among the biggest events of the year, and as a result we usually get to see star studded matches main eventing the show.
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Since it is such an integral event, it is not at all easy getting a spot in the main event of SummerSlam. Only a select few ones get the chance, and even those don't get many chances. However, some wrestlers managed to main event SummerSlam both as a heel and a face.
7 Randy Savage
Randy Savage became the first wrestler to achieve this feat. He achieved it in the first two editions of SummerSlam itself. In 1988, Savage was a face and he teamed up with Hulk Hogan to take on the team of Andre The Giant & Ted DiBiase.
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The following year in 1989, Savage turned heel and feuded with his former partner Hulk Hogan. In the main event of SummerSlam, he was once again in a tag team match as he teamed up with actor Zeus to face Hulk Hogan & Brutus Beefcake
6 Shawn Michaels
Shawn Michaels spent quite some time as both heel and face. His first run as a main eventer started in 1996 as a babyface. In that year, The Heartbreak Kid main evented SummerSlam for the first time retaining his WWE Title against Vader. He had another SummerSlam main event as a face in 2003, as he was part of the main event Elimination Chamber alongside Triple H, Chris Jericho, Goldberg, Randy Orton and Kevin Nash.
Shawn turned heel in late 1997, but had to retire in 1998, and stayed retired until 2002. Thus, he only had one SummerSlam main event as a heel, when he faced Hulk Hogan at SummerSlam 2005. Michaels wasn't a regular heel at the time, he was playing the heel role just for this program. The contest is remembered for wrong reasons, as Shawn was overselling Hogan's moves.
5 Randy Orton
Randy Orton's career in WWE has lasted very long, and he main-evented SummerSlam four times over the course of his career. Three of those main events saw Orton as a heel. As mentioned previously, he was part of the Elimination Chamber which closed SummerSlam 2003. He also challenged for John Cena's WWE Title in the main event of SummerSlam 2007.
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The Viper's sole SummerSlam main event match as a face happened in 2016. At the event, Orton faced Brock Lesnar in a dream match. Lesnar absolutely destroyed Orton with many bare-knuckled elbow strikes, which caused Orton to bleed heavily. Lesnar was thus awarded the win via technical knockout.
4 CM Punk
CM Punk wasn't given the opportunity to main event a lot of PPVs, but he managed to achieve this rare feat. He main evented SummerSlam twice. As a heel, he defeated Jeff Hardy to win the World Heavyweight Title in the main event of SummerSlam 2009.
His SummerSlam main event as a face was at SummerSlam 2011. After John Cena became the new WWE Champion on Raw, the former WWE Champion CM Punk returned. This set up a match at SummerSlam to crown the Undisputed WWE Champion, which Punk won. However, he couldn't close the show as the WWE Champion, as Alberto Del Rio cashed in his Money in the Bank contract and became the WWE Champion.
3 Triple H
Triple H being in this list is not surprising, as he also had a pretty long career and he was part of the main event of four SummerSlams. Three of those main events saw Hunter as a heel. Those years were 1999, 2000 and 2003. All the three were multi-man World Title matches.
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HHH was a heel for most part of his active career, but he turned face towards the end of his career. He ran into a feud with the recently returned Brock Lesnar in 2012, and main-evented SummerSlam against him as a part-timer babyface.
2 Braun Strowman
Braun Strowman main evented just 2 SummerSlam events, but both as different characters. He first main-evented SummerSlam 2017 as a heel as part of a Universal Title Fatal 4-Way match including Brock Lesnar, Samoa Joe and Roman Reigns.
He turned face shortly after the event, and went on to win the Universal Championship in 2020. He then had a long rivalry with Bray Wyatt, and unsuccessfully defended his Universal Title against "The Fiend" in the main event of SummerSlam 2020.
1 Roman Reigns
After The Shield split in 2014, Roman Reigns got a huge babyface push. His first SummerSlam main event as a face was in 2017, when he was part of the Universal Title Fatal 4-Way match. The following year, he once again challenged for the Universal Title as a face against Brock Lesnar and defeated him.
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Roman Reigns finally turned heel in 2020. Since then, he has main evented every SummerSlam edition as a heel. He successfully retained his Universal Title against John Cena and Brock Lesnar in 2021 and 2022, respectively. He's currently a heel and will most likely main event this year's SummerSlam as well.
