If I had to rank the best season for music (whether it's album releases, single releases, or just the quality of songs out at the time) this is how I'd rank them, 1 being best.
1. Fall - No denying this. The holiday season is where sales dramatically pick up. Britney has been releasing her music in the fall for the past couple of years and it works out great. It worked with Gimme More, 3, and Womanizer as singles and with Blackout and Circus as albums. This past fall we had The Fame Monster and Rated R as the major albums of the fall. Bad Romance, 3, and Hard were radio smashes around this time too. Black Friday really does make a difference!
2. Spring - This is a great time of year to release singles (End of March - early June) with a release of an album at the end of May or somewhere in June. Usually these singles taking off at the second half of Spring will be the ones carrying popularity as summer smashes, and they join the fall releases as the biggest and most remembered songs of the year. Poker Face, Right Round, and Boom Boom Pow owned Spring 2009 and the popularity continued into the summer with I Gotta Feeling and LoveGame/Paparazzi.
3. Summer - Usually you can get some moderate hits and albums released mid-summer that have catchy summer vibes, but they're not always the best ones performing on the charts.
The songs that OWN the summer are RELEASED in the SPRING.
4. Winter - Ke$ha hit it big in January, but usually after the Holiday season is the absolute worst time for music sales and releasing new material.
Rank them in your opinion.
