1985 came around and Helloween recorded its first record Helloween, a self-titled EP containing 5 tracks. The EP was successful. During that same year the group recorded and released its first full-length album titled Walls of Jericho which was well-received, with its mixture of speed and melodies redefining heavy metal. (In fact, WWE Wrestler Chris Jericho took his stage name from the album, as well as the name of his signature submission move, Walls Of Jericho). However, during the following tour, it became obvious that Kai had difficulties singing and playing the guitar at the same time. Kai's last recorded performance as the band's lead singer was in 1986 on a single EP titled Judas, which contained the song "Judas" along with some live tracks. After that, Helloween began the search for a new vocalist.
The first choice was to recruit former Tyran' Pace vocalist Ralf Scheepers, who had sung lead for the band on the short "Judas" tour; he declined. The band ended up finding an 18-year-old talent from a local Hamburg band, Ill Prophecy, named Michael Kiske. With their new lead singer in tow, they approached record labels Noise International and RCA and floated the idea of releasing a double-LP to introduce the new line-up. They were turned down. As a result, they recorded Keeper of the Seven Keys, Part 1, which was released in 1987. It established Helloween as one of the most successful heavy metal bands in Europe. In 1988 Helloween released Keeper of the Seven Keys Part II, the companion album and their most famous release featuring the classic line-up. Fortune smiled on the German quintet when MTV put their single "I Want Out" into heavy rotation. Additionally, in support of its "Headbanger's Ball" show, MTV presented the inaugural Headbanger's Ball Tour and invited Helloween as special guests, joining Bay Area thrash-metal band Exodus in support of headliners Anthrax. The band was slotted in the more-prestigious second spot, right before Anthrax's set. On the heels of this exposure to US audiences, the band achieved worldwide success, and things were looking extremely well.
The euphoric highs experienced by the band would quickly lead to one of the darkest periods in its existence. Guitarist Kai Hansen unexpectedly left the band soon after the European leg of the "Keeper 2" tour due to conflicts within the band, troubles with record company Noise International, and a growing dissatisfaction with life on tour. He was quickly replaced by former Rampage guitarist Roland Grapow, who finished the rest of the "Keeper 2" tour with the band.
In 1989 the band released a live album called Live In The UK, featuring live material from their 1988 European tour, entitled "Keepers Live" in Japan and "I Want Out Live" in the U.S. The remaining members continued on, but ran into label problems with Noise, and, after litigation which kept them from touring and releasing new material, were eventually released from their contract. A new album would not appear until 1991 when, after several rumors about the band breaking up, they released the comically entitled Pink Bubbles Go Ape for their new record company, EMI. The album was less heavy, and with song titles such as "Heavy Metal Hamsters"; "I'm Doing Fine, Crazy Man"; and "Shit and Lobster", showed a shift towards, and an emphasis on, humor rather than the epic feel present on previous releases. As a result, Pink Bubbles Go Ape failed both commercially and critically, and soon tensions started to build up amongst the band members.
The pop-influenced follow-up Chameleon, released in 1993, cost the band what hardcore fans they had left. Instead of taking a heavier approach, as fans had clamored for, the band ventured into new territory, eschewing their signature double-guitar harmonies for synthesizers, horns, acoustic guitars, a children's chorus, country music, grunge and swing. As with the previous album, Chameleon failed commercially and critically. Tensions within Helloween worsened, and the band split into three factions, with Michael Kiske and Ingo Schwichtenberg on one side, Michael Weikath and Roland Grapow on the other, and Markus Grosskopf in the middle, trying to keep an uneasy peace between the four men.
Shortly afterwards, the band would begin to disintegrate. During the Chameleon tour, the band would routinely play to half-filled venues, the fans staying away in droves when faced with the prospect of having to sit through a set of nearly all songs off the new album. Worse yet, drummer Ingo Schwichtenberg fell ill due to mental and drug-related issues, and was eventually fired, replaced by session drummer Ritchie Abdel-Nabi. Meanwhile, the conflicts within the rest of the band had reached critical mass, with Michael Weikath refusing to work any longer with Michael Kiske. The decision was made to fire Kiske. In hindsight, it is clear that the move away from power metal to pop was Kiske's idea; he had taken on a more vocal role in the band, and did not hide the fact that he disliked Helloween's style of power metal, instead favoring a softer, pop style of music. Since his firing, Kiske has not spoken positively about Helloween, and still claims to hate the whole heavy metal scene. Kiske would return with a solo album, 1996's Instant Clarity. The album was, for the most part, pop and soft rock, except for "The Calling", co-written by Kiske and Iron Maiden guitarist Adrian Smith, and the Smith-Hansen-Kiske collaboration "New Horizons", the only "heavy metal" songs on the album. Since his first solo effort, Kiske has reinvented himself musically and relegated himself to eclectic-sounding albums such as Readiness to Sacrifice, SupaRed, and the self-titled Kiske; Kiske will also occasionally be a guest singer on other artists' albums, but refuses to be credited by his given name in an effort to prevent being associated with the metal genre. In May 2008 Kiske released Past In Different Ways, an album that featured some of his old Helloween songs, albeit rearranged and re-recorded acoustically.
In addition to the firing of Kiske, Abdel-Nabi, whose inability to replicate Schwichtenberg's machine-gun style of drumming hindered Helloween's ability to play fan-favorites like "Eagle Fly Free" and "How Many Tears" live, was given his walking papers as well. 1993 would come to a disastrous close as, in short, the band had no singer, no drummer, no record contract (EMI let the band go after the horrible returns for Pink Bubbles Go Ape and Chameleon), and seemingly no future.
Helloween returned in 1994, however, with former Pink Cream 69 frontman Andi Deris as their new lead singer, and Uli Kusch, formerly of Kai Hansen's Gamma Ray on the drums. Deris, in fact, had been approached by Weikath to join the band in 1991, but, despite being intrigued by the offer and dealing with emerging conflicts between himself and Pink Cream 69, declined. In the intervening year, however, Kiske was fired from Helloween and the issues within Pink Cream 69 worsened; faced with the inevitability of his firing, Deris accepted Weikath's offer. Despite not possessing the 4-octave range boasted by Kiske, Deris' vocal similarity to Kai Hansen, his enthusiasm, strong songwriting skills and the return of the "classic" Helloween sound in songs like "Where The Rain Grows", "The Game Is On" and "Still We Go", as well as the seeming rejuvenation of Weikath and Grapow, struck a chord with the fans. With this new and recharged lineup, and a new record contract courtesy of Castle Communications, Helloween released their successful comeback album, Master of the Rings. Oddly enough, despite the almost universal hatred toward the Chameleon album, on the Master of the Rings tour, the band played "Giants" at a handful of shows. It was quickly dropped from the setlist; in fact, Helloween has refused to play any of the tracks off Chameleon on any tours from that point forward.
The story of Helloween's return was tempered by tragedy in 1995, as the band, its members and fans were saddened by the suicide of original drummer Ingo Schwichtenberg. In the years since his departure from Helloween, Schwichtenberg had spiraled deeper into drug-use and depression; additionally, he was never able to recover emotionally after being fired from the only band he had ever known. The former drummer committed suicide by jumping in front of a train in his native Hamburg. Dedicated to his memory, 1996's The Time Of The Oath re-established the band as one of the most popular European metal bands (see 1996 in music). Following another world tour, a double live album called High Live was released.
In 1998 Helloween released Better Than Raw, one of the band's heaviest albums since the full-length debut. The subsequent supporting tour was par for the course, with the usual shows in Europe, Japan and Brazil, except for one surprise: On December 20, 1998, the band visited New York and played a show in Coney Island, the first show for Helloween in the United States in nearly a decade. Despite almost zero hype, attendance at the show was respectable, planting the seeds for a future return to the States. The band would follow Better Than Raw with a 1999 release entitled Metal Jukebox, a cover-album featuring Helloween's versions of songs from bands as diverse as Jethro Tull, Faith No More, The Beatles, ABBA and Deep Purple. The year 2000 saw the release of The Dark Ride, a more experimental and darker album than their previous releases, complete with downtuned guitars and a gruffer singing style from Deris.
Immediately following the tour, Helloween parted ways with guitarist Roland Grapow and drummer Uli Kusch. One version of events states that Weikath, Deris and Grosskopf felt that Kusch and Grapow, in particular, were spending more time on and paying more attention to their new side-project, Masterplan, and that because they were not devoted 100% to Helloween they were let go; another version states that Grapow and Kusch had pushed to continue the direction that the band had taken with The Dark Ride and that Weikath, not wanting a repeat of the Kiske situation, huddled with Deris and Grosskopf, whereby the decision was made to get rid of them. In any case, they were fired, via e-mail (with Grapow's wife finding out before he did that he had been fired), and decided to make Masterplan their full-time band, while their replacements were soon found in guitarist Sascha Gerstner (ex-Freedom Call, Neumond), and drummer Mark Cross (ex-Metalium, Kingdom Come, currently in Firewind), culminating with the recording of another studio album, entitled Rabbit Don't Come Easy, in 2003. Cross could not finish the album due to mononucleosis, completing only two tracks; the drum tracks were completed by Motörhead's Mikkey Dee. Stefan Schwarzmann, former drummer of Running Wild and Accept would shortly thereafter take over the drumming duties. Despite a somewhat tepid response to the album, Helloween nonetheless completed a successful world tour, highlighted by the return of classic songs such as "Starlight", "Murderer", "Keeper of the Seven Keys" and "How Many Tears" to the setlist. Additionally, the band toured the United States for the first time since 1989 playing to sold-out crowds at nearly every venue.
2005 saw yet another line-up change following the "Rabbits on the Run" tour as it became apparent that Helloween and Stefan Schwarzmann did not share the same musical vision. As further noted by the band, he had some trouble performing fast drum parts, so he was replaced by Dani Löble, the previous drummer of German metal band Rawhead Rexx And also Tour drummer for Blaze A change in record company also followed as they inked a deal with German label SPV. Any fears that what had now become a revolving door of band members would affect the quality of their new album were laid to rest as Helloween's new studio album, entitled Keeper of the Seven Keys - The Legacy, was released in October 28th, 2005 in Germany, and November 8th in the U.S.A. to commercial and critical acclaim. The album had a pre-release single, Mrs. God, as well as a video for the track. The track Light the Universe was released as a single on November 22nd, featuring Candice Night of Blackmore's Night on guest vocals. She also appears in the video clip for that track.
In late 2006, Helloween filmed and recorded shows in São Paulo (Brazil), Sofia (Bulgaria) and Tokyo (Japan), for their live album Keeper Of The Seven Keys - The Legacy World Tour 2005/2006. The DVD also featured extra footage of the band as well as interviews and a road movie. This is the second Helloween live album to feature Andi Deris as frontman, and third overall. It enjoyed chart success in several countries: Germany: 9 (DVD) & 58 (CD), Sweden: 9 (DVD), France: 10 (DVD).
Helloween has since completed their latest studio album Gambling with the Devil, which was released on October 23, 2007. It has received many positive reviews, with most fans praising the album as being one of the best Deris era albums. Despite being one of Helloween's heavier albums With tracks such as 'Kill it' And 'The bells of the 7 hells', it is noted for featuring more keyboards. "As Long As I Fall",, the first single released in early September is available only via download (save for Japan, where it was released on CD). The video for the song was shot and Directed by Alex Diezinger of AVA Studios And is available at their official site.
Helloween teamed up with Kai Hansen's current band Gamma Ray for the ongoing world tour, entitled Hellish Rock 2007/2008, that started in early November 2007. Helloween are headlining and Gamma Ray are labeled as the "very special guest" with most shows going along fellow German "guest" Axxis. The tour is notable for Kai Hansen stepping on stage with his former band fellows Weikath and Grosskopf to perform hits "I Want Out" and "Future World" in the last encore segment of Helloween set.