In 1994 the band was signed to Castle Communications and got a new vocalist, Andi Deris from Pink Cream 69. The drums were taken up by Uli Kusch, formerly of Gamma Ray. The new line-up soon released Master of the Rings, receiving great reviews. The musical style was turned back in the direction of the Keeper albums and while many fans had some trouble getting used to the voice of Andi Deris, it actually sold pretty well.
The next album, entitled The Time Of The Oath, came out in 1996. The good old Helloween style was back, along with some new fresh aspects like the "Metallica-style" use of rhythm guitar in a few songs. The album did well throughout the world and sold in excess of a million copies. 1996 was also a year of tragedy as Ingo Schwichtenberg committed suicide. The Time Of The Oath was dedicated to the memory of this great drummer. In pace requiescat, Ingo. The Time Of The Oath Tour material was used to record the next live album, High Live. It is a 2-CD bunch of new songs with some of the old favourites thrown in.
A boxed set called the The Pumpkin Box was released in 1998. The compilation contained the best material from years 1985-1993, a 70 page book and a disc featuring interviews with past and present members of the band. The next Helloween record with original content, Better Than Raw, also came out in 1998. The album includes really agressive pieces like Push but also more mellow pieces like Hey Lord! and Time and even one song in Latin. It has received very good reviews and most fans like the album very much. This is no surprise; strong song-writing skills, fiercely potent musicianship, while returning to that brasher attitude the band used to have make it another great piece of Helloween history. Another release this year was a weird one: Karaoke Remix vol. 1 and vol. 2. Intended mostly for the Japanese market, these discs include karaoke versions of Helloween songs. The volume one consists of older songs while the vol. 2 covers the albums from Master of the Rings to Better Than Raw.
1999 saw the release of Metal Jukebox album, which contains cover tracks done in the Helloween fashion. The album is not a typical metal cover album with 70's and 80's metal and punk songs, some of the songs are written well before metal music was around. For example Space Oddity (David Bowie), Lay All Your Love On Me (Abba), He's a Woman She's a Man (Scorpions) are included, with 9 other songs.
The Dark Ride was released in October 2000 and it was special. The album combines modern elements with the old Helloween style. Most of the lyrics have a somewhat dark element to them with a lot of depth and meaning. The album is said to be the best produced Helloween album ever. If you are into melodic metal, you should definitely give it a go!
The album Rabbit Don't Come Easy (2003) brought more changes to the band's line-up. Long-time guitarist Roland Grapow and drummer Uli Kusch left to form a new band called Masterplan and were replaced by Sascha Gerstner (guitar, ex-Freedom Call member) and Stefan Schwarzmann (drums, ex-Running Wild, U.D.O., Accept). Many songs on the album share the sinister tones of The Dark Ride but the ones written by Sascha Gerstner bring back some of the old "happy Helloween" atmosphere. The lighter side was present on The Dark Ride too but on this album is seems to be gaining even more momentum.