January – Slick is hospitalized with a suspected throat growth, undergoing a csecond operation for nodes on her vocal cords.

April – Live album, Bless Its Pointed Little Head, recorded at the Fillmore West on October 24-26th, 1968, and the Fillmore East, November 28-30th, 1968, makes #17 in the US.

May – Casady is arrested for possession of marijuana, in New Orleans, and will receive a 2 1/2 year suspended sentence.

June – Bless Its Pointed Little Head becomes the group’s first UK chart entry, spending a week at #38.

August – The band performs at the “Atlantic City Pop Festival”, Atlantic City, NJ, before an audience of 110,000.
The group headlines a concert in Tanglewood, Lenox, MA with B.B. King and The Who.
Airplane headlines the second day, by now early Sunday morning, of the “Woodstock Music & Art Fair”, Bethel, NY.

October – Kantner is busted for marijuana possession in Honolulu, HI, found guilty of a misdemeanor and fined $350.

November – The group plays at the Fillmore East, with Slick dressed as Hitler and actor Rip Torn making an appearance as Richard Nixon. Also performs the  “First (and last) Annual Palm Beach International Music and Arts Festival in late November, 1969.”

December – Volunteers, the band’s most overtly political work, reaches #13 in the US.
The band takes part in the Rolling Stones’ ill-fated concert at Altamont Speedway, CA. Balin is attacked halfway through a song, by one of the Hell’s Angels “handling” security.
The extracted title track, Volunteers, makes #65 in the US.
The group plays a New Year’s Eve show at the Winterland Ballroom in San Francisco.