Systems and methods for synchronizing playing of content with future events

A system comprising:

• control circuitry configured to:
• identify a playlist comprising a plurality of content items having a plurality of durations, respectively;
• identify a future time at which a time-sensitive content item of the plurality of content items is to be played;
• identify a plurality of modifiability scores for the plurality of content items;
• determine an estimated playback time of the time-sensitive content item, based at least in part on the plurality of durations;
• determine that the estimated playback time is different from the identified future time;
• modify the playlist by modifying a duration of at least one content item of the plurality of content items to synchronize the estimated playback time of the time-sensitive content item with the identified future time, based at least in part on the plurality of modifiability scores and a difference between the estimated playback time and the identified future time;
• and
• cause the modified playlist to be played, including causing the time-sensitive content item to be played at a time such that the time-sensitive content item is playing when the future time becomes a present time.