He was a Glaswegian living and working in London, first appeared aged 35 on Countdown midway through Series 21, defeating Nick Saloman 62 – 53 on his debut on 14 February 1991. Grossman won four more games before losing his 6th to Gillian Tickle 54 – 51, but his scores were high enough to ensure him a place in the final rounds as #3 seed. He defeated Adam Simmons in the quarter-final, before 'gaining revenge' by defeating Gillian Tickle 59 – 44 in the semi-final. Despite having his first word disallowed, Grossman dominated the final against Jackie McLeod, winning 99 – 67 to become the 21st series champion.
He returned to Countdown in 2013, as one of 41 contestants taking part in the 30th Birthday Championship. He won his first match in a rematch of the Series 21 final against Jackie McLeod by a score of 79 – 65, before losing to Series 6 champion Darryl Francis on a crucial conundrum.
Grossman is also a Scrabble expert, and has appeared under a different name on Fifteen to One. He has also written several books on Scrabble, including Scrabble: Play to Win and 101 Ways to Win at Scrabble.
|#||Date||Type||Contestant 1||Score||Contestant 2||Guest||Lex||Max|
|1101||14/02/1991||P||Nick Saloman||53 – 62||Barry Grossman||Simon Williams||Alexandra Clayton||74|
|1102||15/02/1991||P||Beatrice Syms||44 – 48||Barry Grossman||Richard Stilgoe||Alexandra Clayton||71|
|1103||18/02/1991||P||Dave Dinsmore||20 – 49||Barry Grossman||Richard Stilgoe||Alexandra Clayton||73|
|1104||19/02/1991||P||Val Carter||35 – 69||Barry Grossman||Richard Stilgoe||Alexandra Clayton||70|
|1105||20/02/1991||P||Richard Foster||34 – 47||Barry Grossman||Richard Stilgoe||Alexandra Clayton||70|
|1106||21/02/1991||P||Gillian Tickle||54 – 51||Barry Grossman||Richard Stilgoe||Alexandra Clayton||70|
|1128||25/03/1991||QF||Adam Simmons||23 – 60||Barry Grossman||Brian Johnston||Richard Samson||75|
|1131||28/03/1991||SF||Gillian Tickle||44 – 59||Barry Grossman||Brian Johnston||Richard Samson||74|
|1132||29/03/1991||GF||Jackie McLeod||67 – 99||Barry Grossman||Sally James, Brian Johnston||Richard Samson||117|
|1331||7/01/1993||CQF||Barry Grossman||50 – 55||Robert Teuton||Richard Stilgoe||Susie Dent||72|
|1870||30/10/1996||cQF||Barry Grossman||48 – 42||Robert Violett||June Whitfield||Susie Dent||84|
|1873||4/11/1996||cSF||Barry Grossman||52 – 51||Brian Hudson||Geoffrey Durham||Susie Dent||70|
|1874||5/11/1996||cF||Barry Grossman||37 – 44||Harvey Freeman||Geoffrey Durham||Susie Dent||73|
|5621||15/01/2013||30BP||Jackie McLeod||65 – 79||Barry Grossman||Martin Lewis||Susie Dent||119|
|5638||7/02/2013||30B1||Darryl Francis||82 – 63||Barry Grossman||Kate Adie||Susie Dent||118|