Olivia was discovered by the director of "Rising Productions" (Vision Factory) while attending the Okinawa Actors' School, subsequently signing to Avex Trax as part of the Japanese idol group D&D. Famed producer Tetsuya Komuro heard of Olivia one day and decided that she would be perfect for a project in which he was planning along with Jean Michel Jarre. The project was to create the theme song for the 1998 FIFA World Cup entitled Together Now. The single was released a month after D&D's first and only album. It was then decided that D&D would disband and be separated into two different groups: 'OLIVIA' as Olivia's solo-project and Aya & Chika as Aya & Chika from D&D.
In 1999 and 2000, Olivia would release six singles, all with a pop-rock sound. Toward the end of 2000, she released her first solo album, synchronicity, which contained all singles released to date, five previously unheard tracks, and one bonus track. It would peak at the number twenty position on the Oricon Charts.
After a hiatus of more than a year, Olivia began to take control of her career, releasing her seventh single Sea me on December 12, 2001. This single marks her switch to one of Avex Trax's sub-labels, cutting edge, from which she continues to release singles and albums. Her releases would become increasingly rare and sporadic from then on, with a Video Clips Collection being issued four months later.
Olivia's next single, Into The Stars, was planned to be released in July of 2002 with an album released at the end of the year. However, plans were changed as the single was postponed until September due to market forces and the album release similarly delayed.
Alongside this, Olivia decided to launch a rare-items fashion label called Black Daisy Ville with her friend Friedia Niimura (Rin Kozue). This fashion line would continue until the summer of 2004 in which a line of clothes and items were released. Friedia would then move to the United States and the line would be discontinued.
Then in 2004, she released her second album The Lost Lolli. This album primarily featured the best material from her four mini-albums and introduced two new tracks, "Alone in Our Castle" and "Fake Flowers" as well as two re-arrangements. The album was released nation-wide with a limited first press version available at Tower Records Japan "SpidERSpins (Lost Lolli Mix)" would be used as a promotional radio single and video for the release. The Lost Lolli would only peak at #111 on the Oricon Charts. However, despite the moderate success of the album, Avex Trax released an overseas version of this album, reflecting Olivia's increasing success outside of Japan. Typically, only chart-topping artists release overseas versions of their albums.
During March 2006, it was announced that Olivia would once again be releasing music in the Japanese music industry. She would provide vocals for the lead vocalist Reira Serizawa in the fictional band Trapnest as a part of the anime adaptation of NANA. She would produce songs for the anime under the alias OLIVIA inspi' REIRA (TRAPNEST) alongside fellow Avex artist, Anna Tsuchiya, whom plays the role of Nana Osaki, the vocalist for Trapnest's rival band Black Stones.
The manga's author, Ai Yazawa, asked Olivia to sing for the anime when a staff member at Avex gave her a copy of Olivia's singles Sea me and Into The Stars. It is reported that she exclaimed, "It can only be her!" when she first heard the music. a little pain would be Olivia's first release for this role in which she first made the general theme to the lyrics, then wrote the song in English. Later on, the lyrics would be changed to Japanese. The single is about "Reira's loneliness, pain and strength," as Olivia found that she could relate well to the character.
Olivia has said that her musical expression has now changed, that the hiatus was because at the time of The Lost Lolli's release, she was "feeling pretty depressed", and "started to notice and realize a lot of her faults"and that her style "has gotten a lot more detailed", it's "pleasing to the ear" and "a lot cooler". She had to do a lot of research into Reira's character, as she "never really read manga". a little pain is specifically tailored to the point of view of Reira. She states, "It was fun to sing as another person. Like an actress. I wrote the lyrics with the image that Reira looked to herself and wrote it. But because she's Reira she has to help all around her and that’s why it seems as though she sings for everyone, but really she sings for herself. I wrote it with that idea in my mind."
When a little pain was first released, it reached a position of number eight on the Oricon Charts, her first top ten position, and two positions below Anna Tsuchiya's single, rose, which had been released on the same day. After the second week, this single had outsold the total sales for her debut single, I.L.Y.~Yokubou~ which was her highest selling single to date at the time.
Olivia would continue to release NANA-related material throughout 2006. The next opening and ending theme songs used after Anna Tsuchiya's rose and Olivia's a little pain were both songs by Olivia. The single Wish / Starless Night, was released in October and peaked at number seven on the Oricon Charts. Following the success of these releases, Olivia's first US appearance was scheduled for the animation convention Pacific Media Expo held in Los Angeles, California in October 2006.
NANA BEST, another compilation album, was released shortly thereafter. This album featured the hit songs from the anime and one unreleased song by both Olivia and Anna Tsuchiya. Olivia and Anna would go on to perform these songs together live at Shibuya AX in March 2007.
July 6, 2007, Olivia held a concert in Paris, France at the popular venue, La Locomotive singing songs from OLIVIA inspi' REIRA (TRAPNEST), The Lost Lolli and The Cloudy Dreamer. She would also make a special guest appearance at the Japan Expo on July 6 and 7.
A new song, 'Bleeding Heart' - a collaborative effort with her brother, Jeffrey Lufkin, was produced for the Vision Factory compilation album FLOWER FESTIVAL～VISION FACTORY presents. The compilation album contains songs set to the theme of 'flowers' by various other artists such as Lead, FUNGO, and hiro. It was released on March 19, 2008
Olivia is released her sixth mini album, "Trinka Trinka", on September 17. which features a new song called "RAIN", which is being used as the new ending theme to K-tai Investigator 7, as well five previously unheard tracks. The album also features the highly anticipated song "Real Love" which was premiered during her concert in Paris. The track, however was renamed as Your Smile and is the last track on the mini album.