Raw and ECW (2005–2008)
On November 1, 2005, he made an appearance at WWE's Taboo Tuesday. Styles was brought in to fill-in for Jonathan Coachman, as Coachman had a match against Batista. Styles joined WWE's Raw as a play-by-play announcer on November 7. On December 4, 2005, it was confirmed by WWE.com that Styles signed a five-year contract to be the official play-by-play commentator for Raw. This would be the first time in Styles' career that he would work in wrestling full-time.
In an earlier interview done by WWE.com, he mentioned that becoming the voice of Raw was a childhood dream come true. Styles also stated that calling WrestleMania was one of his lifelong dreams growing up. However, despite being the lead announcer for Raw, it was announced that he would not provide commentary for WrestleMania 22, which instead featured Jim Ross calling the matches for Raw. Styles learned that he would not be announcing at WrestleMania 22 when he arrived on Raw on March 27, 2006. The reason for Styles not calling the event is that Vince McMahon disliked pure play-by-play announcing and wanted a "storyteller" instead.
Jim Ross had a similar problem when he first joined WWE, and Styles has credited Ross for teaching him the WWE style of commentary upon his return. However, Styles was present at WrestleMania 22, losing his "WrestleMania virginity" as he put it, calling the Hardcore Match between Mick Foley and Edge. This was Styles' idea, as he wanted to achieve his lifelong dream of calling a match at WrestleMania and pitched the idea to Vince McMahon by explaining that he had called more Hardcore/ECW style matches than any other announcer in history.
On the May 1, 2006 edition of Raw, Styles announced that he was quitting by delivering a worked shoot promo, in which he bashed Vince McMahon, WWE, sports entertainment, and the fact that people "buy into this crap". To further the storyline, his profile was removed from both the Raw superstars section and the ECW One Night Stand subsite. Styles remained under contract with WWE after he quit Raw; however, making his next appearance at WWE vs. ECW Head-to-Head. Here, he provided commentary with Tazz and announced that (now former ECW Representative) Paul Heyman had reinstated him as commentator of the new ECW brand of WWE. He provided commentary for ECW One Night Stand 2006 on June 11 and went on to announce ECW's weekly show on Sci-Fi Channel. In April 2008, Styles began working on WWE.com, with Mike Adamle replacing him as ECW's play by play commentator. He stated repeatedly that he had retired from announcing full-time and was thrilled to continue to work for WWE as Director of Digital Media Content. Styles was soon after promoted to Vice President of Digital Media Content.
As Vice President of Digital Media Content,[7] Styles worked on WWE.com and the WWE app, writing and editing as well as working closely with WWE's sales and sponsorship division. Additionally, Styles hosted a show called Oh My God! Moment of the Week[8] that ran from September 2008 to December 2008. On the December 8, 2008 episode of Raw, Styles presented the "O M G!" Moment of the Year award at the 2008 Slammy Awards with Alicia Fox, saying his famous "Oh My God!" catchphrase.
In 2010, Styles' announcing contract expired, but he remained with WWE as a non-contracted employee and continued to host "History of ECW" on WWE Classics On Demand TV service until it was discontinued in January 2014 because of the launch of WWE Network. Episodes of ECW Hardcore TV which aired in syndication from 1993 to 2000 and was hosted and announced by Styles are available on WWE Network along with all ECW pay-per-views. Due to music licensing issues, some of the commentary by Styles from ECW pay-per-views on the WWE Network has been re-recorded by Styles. Styles continued to host the ECW Unreleased WWE home video series. On November 11, 2014, Styles and Paul Heyman hosted WWE Network special ECW Exposed.[9]
Styles appeared in WWE 2K16, announcing an ECW match between Steve Austin and Mikey Whipwreck in the Austin 3:16 showcase.
On August 8, 2016, it was reported that Styles was released from WWE and returned to advertising sales in New York City.