Diana Krall: How Nanaimo's Piano Prodigy Became the World's Biggest Jazz Singer

The data box: Krall in numbers

Diana Krall by the numbers - Born: November 16, 1964, Nanaimo, BC — started piano at four, performed in restaurants by her teens. - Training: Berklee College of Music, then New York, studying with the legendary pianist Jimmy Rowles. - Breakthrough: All for You (1996) — a Nat King Cole tribute that earned a Grammy nomination and international notice. - The crossover: When I Look in Your Eyes (1999) — a Grammy for Best Jazz Vocal Performance and a nomination for Album of the Year, an almost unheard-of showing for a jazz vocal record. - Sales: Multiple platinum albums across the 2000s; the best-selling jazz vocalist of her generation. - Honors: Multiple Junos, a star on Canada's Walk of Fame, and the Order of Canada.

Chapter one: the Nanaimo years

Krall's childhood was music-saturated: a father with a vast record collection, a living-room piano, and the Vancouver Island jazz scene as a backdrop. She absorbed standards the way other kids absorbed pop radio, and by her teens she was gigging professionally — the rare child who turned a household hobby into conservatory discipline, then a scholarship to Berklee.

Chapter two: apprenticeship

Berklee gave her technique; New York gave her depth. Studying with Jimmy Rowles — one of jazz piano's great accompanists — Krall learned the secret that would define her art: restraint. Where virtuosos show off, Krall listens. Her piano playing breathes behind her voice, and her voice — husky, unhurried, and slightly behind the beat — makes every lyric sound confessed rather than performed.

Chapter three: the records

The albums arrived steadily through the 90s — Stepping Out (1993), Only Trust Your Heart (1995) — but All for You (1996) was the breakthrough: a full-album Nat King Cole tribute that critics embraced and that announced a major artist. Love Scenes (1997) went platinum in Canada; When I Look in Your Eyes (1999) made her a household name, earning her the Grammy and the rare Album of the Year nomination that announced jazz could still compete in the mainstream. The follow-up, The Look of Love (2001), went platinum and topped jazz charts worldwide.

Chapter four: superstardom and the private life

Through the 2000s, Krall did what no jazz singer had done in decades: she filled concert halls and sold millions of records while staying true to the standards repertoire. Live in Paris (2002) captured the peak of her stage powers and won another Grammy. In 2003 she married Elvis Costello — a partnership of two of the most distinctive interpreters in music — and they became parents to twin sons in 2006, balancing family life with two relentless careers. Her 2010s work ranged widely: Glad Rag Doll (2012) dug into Prohibition-era material; Wallflower (2015) reimagined 70s pop songs as standards; Turn Up the Quiet (2017) and This Dream of You (2020) returned to the classic repertoire with an elder's gravity.

The Krall-Costello partnership

It's worth pausing on the marriage: two of the era's most distinctive interpreters, one from jazz standards and one from new-wave literati, building a life between Nanaimo, New York, and London. They've collaborated musically too — Costello co-wrote material on The Girl in the Other Room (2004) — and their twin sons have grown up backstage at both parents' tours. For fans of either artist, the pairing is a reminder that taste travels: the punk-adjacent songwriter and the standards singer found common ground in the American songbook's grammar of wit and heartbreak.

Why Diana Krall matters

1. She carried jazz into the mainstream single-handedly. In an era when the industry declared vocal jazz dead, Krall sold out symphony halls.
2. She's a pianist first. Her trio interplay ranks with the great accompanists; the singing is only half the instrument.
3. She never left the music. Through fame, marriage, motherhood, and loss, the records keep coming — each one an argument for patience in an impatient industry.

Where she sits in the canon

Call her the most commercially successful Canadian jazz artist in history and the claim holds. Oscar Peterson was the greater pianist, but he never moved units like Krall; no Canadian vocalist in any genre has carried a standards repertoire to bigger audiences with the music's dignity intact. She's also the bridge generation — the artist who proved that an audience raised on rock would still show up for Cole Porter if the singer was good enough, paving the road for Diana's descendants from Michael Bublé (her compatriot in the standards revival) to the jazz-adjacent artists of the streaming era. Nanaimo's finest export isn't a singer who happened to play piano. It's a pianist who happens to own the songbook.